Arylisoxazoline derivatives, processes for their preparation and their use as pesticides

ABSTRACT

Arylisoxazoline derivatives, processes for their preparation and their use as pesticides  
     Compounds of the formula (I),  
                 
 
     in which the symbols and indices are as defined below:  
     X is identical or different  
     a) halogen, cyano, nitro;  
     b) (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylsulfinyl, where the radicals of group b are unsubstituted or substituted by one or more, preferably one, two or three, radicals selected from the group consisting of halogen;  
     R 1  is identical or different halogen, (C 1 -C 4 )-haloalkyl,  
     (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy or cyano;  
     m is 0, 1, 2 or 3;  
     n is 1, 2, 3, 4 or 5;  
     Z is oxygen, sulfur, CH 2 or NR 2 ;  
     R 2  is CN, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, CHO, (C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkoxycarbonyl or (CW)NR 3 R 4 ;  
     R 3 , R 4  are identical or different H, (C 1 -C 6 )-alkyl;  
     W is O or S;  
     G is mono- to tetrasubstituted, preferably mono- or disubstituted, isoxazoline which is attached in the 3-, 4- or 5-position to the adjacent phenyl ring;  
     their pure isomers (optical and geometrical isomers), isomer mixtures and N-oxides are suitable for use as pesticides.

[0001] The invention relates to arylisoxazoline derivatives, to processes for their preparation, to compositions comprising them and to their use for controlling animal pests, in particular arthropods, such as insects and Acarina, and helminths.

[0002] Owing to their biological activity, certain 1,3-oxazolines, 1,3-thiazolines, pyrrolines and imidazolines are suitable for controlling animal pests (see, for example, WO-A-93/24470, WO-A-95/04726 and WO-A-96122283).

[0003] However, owing to the multifarious requirements that modern pesticides have to meet, for example with respect to efficacy, persistency, activity spectrum, use spectrum, toxicity, combination with other active compounds, combination with formulating agents or synthesis, and owing to the possible occurrence of resistance, the development of such substances can never be considered to be concluded, and there is a constant great need for novel compounds which, at least in some aspects, offer advantages compared to the known compounds.

[0004] It was an object of the present invention to provide compounds which, under various aspects, widen the spectrum of pesticides.

[0005] This object and other objects which have not been explicitly mentioned, which can be derived or deduced from the contexts discussed here, are achieved by arylisoxazoline derivatives of the formula (I),

[0006] in which the symbols and indices are as defined below:

[0007] X is identical or different

[0008] a) halogen, cyano, nitro;

[0009] b) (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl, where the radicals of group b are unsubstituted or substituted by one or more, preferably one, two or three, radicals selected from the group consisting of halogen;

[0010] R¹ is identical or different halogen, (C₁-C₄)-haloalkyl,

[0011] (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy or cyano;

[0012] m is 0, 1, 2, 3 or 4;

[0013] n is 1, 2, 3, 4 or 5;

[0014] z is oxygen, sulfur, CH₂or NR²;

[0015] R² is CN, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, CHO, (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkoxycarbonyl or (CW)NR³R⁴;

[0016] R³, R⁴ are identical or different H, (C₁-C₆)-alkyl;

[0017] W is O or S;

[0018] G is mono- to tetrasubstituted, preferably mono- or disubstituted, isoxazoline which is attached in the 3-, 4- or 5-position to the adjacent phenyl ring;

[0019] their pure isomers (optical and geometrical isomers), isomer mixtures, N-oxides and salts suitable for use as pesticides.

[0020] Surprisingly, compounds of the formula (I) have, with respect to the activity spectrum and the potency, better acaricidal and insecticidal action than known 1,3-oxazoline, 1,3-thiazoline, pyrroline or imidazoline derivatives.

[0021] The symbols and indices in formula (I) preferably have the following meanings:

[0022] X is preferably halogen, in particular Cl, Br or F, cyano, nitro, (C₁-C₄)-alkyl, (C₁-C₃)-haloalkyl, (C₁-C₄)-alkoxy or (C₁-C₃)-haloalkoxy.

[0023] X is particularly preferably halogen, in particular Cl, Br or F, (C₁-C₄)-alkyl, (C₁-C₃)-haloalkyl, (C₁-C₄)-alkoxy or (C₁-C₃)-haloalkoxy.

[0024] m is preferably 0 or 1.

[0025] n is preferably 1, 2 or 3.

[0026] Z is preferably oxygen or CH₂.

[0027] R¹ is preferably H, halogen, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy.

[0028] G is preferably

[0029] t is 0,1, 2 or 3, preferably 0 or 1.

[0030] R⁵ is identical or different

[0031] a) halogen, CN, NO₂;

[0032] b) a straight-chain or branched alkyl group having 1 to 12 carbon atoms, where one or more (CH₂) groups are optionally replaced by —O—, —S(O)—_(0,1,2), —NH—, —NR⁶—, —GO—, —Cs—, —CH═CH—, —C≡C—, unsubstituted or substituted aryidiyl, unsubstituted or substituted heterocyclyidiyl, unsubstituted or substituted (C₃-C₈)-cycloalkanediyl or unsubstituted or substituted (C₃-C₈)-cycloalkenediyl, with the proviso that chalcogens may not be adjacent to one another, where two radicals R⁵ together with the atoms of the isoxazoline ring optionally form a 3- to 8-membered ring system and where individual hydrogen atoms are optionally replaced by halogen;

[0033] c) in the case of two radicals R⁵ located in the α-position, the radicals are also (═Y), where Y is (═O), (═S), (═NOR⁶) or (═CR₂ ⁶);

[0034] with the proviso that the radical(s) R⁵ together do not comprise more than one ring system having five or more members.

[0035] R⁶ is (C₁-C₄)-alkyl, unsubstituted or substituted phenyl or unsubstituted or substituted benzyl.

[0036] As substituents on the isoxazoline radical, the radicals R⁵ preferably have the following meanings:

[0037] R⁵ is identical or different D-R⁷, or two radicals R⁵ together with the atoms to which they are attached form a three to eight-membered saturated or unsaturated ring system which is unsubstituted or substituted by one or more radicals R⁷ and which optionally also contains further heteroatoms, preferably O, N, S, SO and/or SO₂;

[0038] D is a direct bond or (C₁-C₆)-alkanediyl, unsubstituted or substituted by one or more halogen atoms;

[0039] R⁷ is identical or different R⁸, R⁹, —C(W)R⁸, —C(═NOR⁸)R⁸,

[0040] —C(═NNR⁸ ₂)R⁸, —C(═W)OR⁸, —C(═W)NR⁸ ₂, —OC(═W)R⁸,

[0041] —OC(═W)OR⁸, —NR⁸C(═W)R⁸, —N[C(═W)R⁸]₂, —NR⁸C(═W)OR⁸,

[0042] —C(═W)NR⁸—NR⁸ ₂, —C(═W)NR⁸—NR⁸[C(═W)R⁸], —NR⁸—C(═W)NR⁸ ₂,

[0043] —NR⁸—NR⁸C(═W)R⁸, —NR⁸—N[C(═W)R⁸]₂, —N[(C═W)R⁸]—NR⁸ ₂,

[0044] —NR⁸—N[(C═W)WR⁸], —NR⁸[(C═W)NR⁸], —NR⁸(C═NR⁸)R⁸,

[0045] —NR⁸(C═NR⁸)NR⁸ ₂, —O—NR⁸ ₂, —O—NR⁸(C═W)R⁸, —SO₂NR⁸ ₂,

[0046] —NR⁸SO₂R⁸, —SO₂OR⁸, —OSO₂R⁸, —OR⁸, —NR⁸ ₂, —SR⁸, —SiR⁸ ₃,

[0047] —PR⁸ ₂, —P(═W)R⁸ ₂, —SOR⁸, —SO₂R⁸, —PW₂R⁸ ₂, —PW₃R⁸ ₂ or two radicals R⁷ together are (═Y), (═N—R⁸), (═CR₂ ⁸) or (═CHR⁸);

[0048] W is O or S;

[0049] R⁸ is identical or different H, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyl, (C₄-C₈)-cycloalkenyl-(C₂-C₄)-alkenyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyl, aryl, heterocyclyl;

[0050] where the radicals mentioned are unsubstituted or substituted by one or more radicals R⁹ and optionally two radicals R⁸ together form a ring system;

[0051] R⁹ is identical or different halogen, cyano, nitro, hydroxyl, thio, amino, (C₁-C₆)-alkanoyl, (C₂-C₆)-haloalkanoyl, (C₁-C₆)-alkoxy, (C₃-C₆)-alkenyloxy, (C₃-C₈)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₃-C₆)-haloalkenyloxy, (C₃-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkoxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkoxy, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyloxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyloxy, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkoxy, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyloxy, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyloxy, (C₁-C₄)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₄)-alkoxy-(C₃-C₆)-alkenyloxy, carbamoyl, (C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₃-C₈)-mono- or dicycloalkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₃-C₈)-cycloalkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₃-C₈)-cycloalkanoyloxy, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, C(O)NH(C₁-C₆)-alkyl, C(O)NH(C₁-C₆)-haloalkyl, C(O)N[(C₁-C₆)-alkyl]₂, C(O)N[(C₁-C₆)-haloalkyl]₂, (C₂-C₆)-alkeneamido, (C₃-C₈)-cycloalkaneamido, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkaneamido, (C₁-C₆)-alkylthio, (C₃-C₆)-alkenylthio, (C₃-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₃-C₆)-haloalkenylthio, (C₃-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkylthio, (C₄-C₈)-halocycloalkenylthio, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylthio, (C₃-C₈)-cycloalkyl-(C₃-C₄)-alkenylthio, (C₄-C₈)-cycloalkenyl-(C₃-C₄)-alkenylthio, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylthio, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylthio, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₃-C₆)-alkenylsufinyl, (C₃-C₆)-alkynylsurlinyl, (C₁-C₆)-haloalkylsulfinyl, (C₃-C₆)-haloalkenylsulfinyl, (C₃-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalkylsulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfnyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfinyl, (C₃-C₈)-cycloalkyl(C₃-C₄)-alkenylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₃-C₄)-alkenylsulfinyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfinyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₃-C₆)-alkenylsulfonyl, (C₁-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₃-C₈)-haloalkenylsulfonyl, (C₃-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalkylsulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfonyl, (C₃-C₈)-cycloalkyl-(C₃-C₄)-alkenylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₃-C₄)-alkenylsulfonyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfonyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₁-C₆)-dialkylamino, (C₁-C₆)-alkylamino, (C₃-C₆)-alkenylamino, (C₃-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₃-C₆)-haloalkenylamino, (C₃-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkamino, (C₄-C₈)-halocycloalkenylamino, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylamino, (C₃-C₈)-cycloalkyl-(C₃-C₄)-alkenylamino, (C₄-C₈)-cycloalkenyl-(C₃-C₄)-alkenylamino, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylamino, (C₂-C₈)-alkenyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylamino, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylamino, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylamino, (C₁-C₆)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, aryl-(C₁-C₄)-alkoxy, aryl-(C₁-C₆)-alkanoyl, aryl-(C₃-C₄)-alkenyloxy, aryl-(C₁-C₄)-alkylthio, aryl-(C₂-C₄)-alkenylthio, aryl-(C₁-C₄)-alkylamino, aryl-(C₃-C₄)-alkenylamino, aryl-(C₁-C₆)-dialkylsilyl, diaryl-(C₁-C₆)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl, where the cyclic radicals are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, thio, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₈)-cycloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylamino, (C₁-C₄)-haloalkylamino and (C₁-C₄)-alkanoyl.

[0052] Particularly preferably,

[0053] R⁵ is CN, unsubstituted or substituted phenyl, unsubstituted or substituted phenoxy, (C₁-C₆)-alkyl, (C₁-C₆)-alkenyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-haloalkenyl, -(C₁-C₆)-alkanediyl-aryl, where the aryl group is unsubstituted or substituted and where one —CH₂ unit is optionally replaced by —C(O)—NR¹⁰—, NR¹⁰—(CO), NR¹⁰ or O.

[0054] R¹⁰ is H, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, unsubstituted or substituted phenyl, unsubstituted or substituted benzyl.

[0055] Particularly preferred for

[0056] are the groups

[0057] Particularly preferred groups of compounds of the formula (I) are those of the formulae (I1) to (I28):

[0058] In the above formula, “halogen” is to be understood as meaning a fluorine, chlorine, bromine or iodine atom;

[0059] the term “(C₁-C₄)-alkyl” is to be understood as meaning an unbranched or branched hydrocarbon radical having 1 to 4 carbon atoms, such as, for example, the methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radical;

[0060] the term “(C₁-C₆)-alkyl” is to be understood as meaning the abovementioned alkyl radicals and also, for example, the pentyl, 2-methylbutyl, 1,1-dimethylpropyl or the hexyl radical;

[0061] the term “(C₁-C₆)-alkanediyl” is to be understood as meaning an unbranched or branched alkanediyl radical having 1 to 6 carbon atoms, such as methylene, ethane-1,2-diyl, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, butane-1,3-diyl or 2-methylpropane-1,3-diyl;

[0062] the term “(C₁-C₄)-haloalkyl” is to be understood as meaning an alkyl group mentioned under the term “(C₁-C₄)-alkyl” in which one or more hydrogen atoms are replaced by the abovementioned halogen atoms, preferably chlorine or fluorine, such as, for example, the trifluoromethyl group, the 1-fluoroethyl group, the 2,2,2-trifluoroethyl group, the chloromethyl or fluoromethyl group, the difluoromethyl group or the 1,1,2,2-tetrafluoroethyl group;

[0063] the term “(C₃-C₈)-cycloalkyl” is to be understood as meaning, for example, the cyclopropyl, cyclobutyl or cyclopentyl group; and also the cyclohexyl, cycloheptyl or cyclooctyl radical;

[0064] the term “(C₃-C₈)-halocycloalkyl” is to be understood as meaning one of the (C₃-C₈)-cycloalkyl radicals listed above, in which one or more, in the case of fluorine optionally also all, hydrogen atoms are replaced by halogen, preferably fluorine or chlorine, such as, for example, the 2,2-difluoro- or 2,2-dichlorocyclopropane group or the fluorocyclopentane radical;

[0065] the term “(C₂-C₄)-alkenyl” is to be understood as meaning, for example, the vinyl, allyl, 2-methyl-2-propenyl or 2-butenyl group;

[0066] the term “(C₂-C₄)-haloalkenyl” is to be understood as meaning a (C₂-C₄)-alkenyl group in which some of, or in the case of fluorine also all, the hydrogen atoms are replaced by halogen, preferably fluorine or chlorine;

[0067] the term “(C₂-C₄)-alkynyl” is to be understood as meaning, for example, the ethynyl, propargyl, 2-methyl-2-propynyl or 2-butynyl group;

[0068] the term “(C₂-C₆)-alkynyl” is to be understood as meaning, for example, the abovementioned radicals and also, for example, the 1-pentynyl, 2-pentynyl, 3-pentynyl, or the 4-pentynyl group;

[0069] the term “haloalkynyl” is to be understood as meaning an alkynyl group in which some of, in the case of fluorine also all, the hydrogen atoms are replaced by halogen atoms, preferably fluorine or chlorine;

[0070] the term “(C₁-C₄)-alkanoyl-(C₁-C₄)-alkyl” is to be understood as meaning, for example, an acetylmethyl, propionylmethyl, 2-acetylethyl or a butyrylmethyl group;

[0071] the term “(C₁-C₄)-alkanoyl” is to be understood as meaning, for example, the formyl, acetyl, propionyl, 2-methylpropionyl or butyryl group;

[0072] the term “(C₁-C₆)-alkanoyl” is to be understood as meaning the above-mentioned radicals and also, for example, the valeroyl, pivaloyl or hexanoyl group;

[0073] the term “(C₂-C₆)-haloalkanoyl” is to be understood as meaning a (C₂-C₆)-alkanoyl group in which some of, in the case of fluorine also all, the hydrogen atoms are replaced by halogen atoms, preferably fluorine or chlorine;

[0074] the term “(C₁-C₆)-alkoxycarbonyl” is to be understood as meaning, for example, the methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl or hexyloxycarbonyl group;

[0075] the term “(C₁-C₆)-haloalkoxycarbonyl” is to be understood as meaning a (C₁-C₆)-alkoxycarbonyl group in which one or more, in the case of fluorine optionally also all, hydrogen atoms are replaced by halogen, preferably fluorine or chlorine;

[0076] the term “(C₁-C₆)-alkylthio” is to be understood as meaning an alkylthio group whose hydrocarbon radical has the meaning given under the term “(C₁-C₆)-alkyl”;

[0077] the term “(C₁-C₆)-haloalkylthio” is to be understood as meaning a (C₁-C₆)-alkylthio group in which one or more, in the case of fluorine optionally also all, hydrogen atoms of the hydrocarbon moiety are replaced by halogen, in particular chlorine or fluorine;

[0078] the term “(C₁-C₆)-alkylsulfinyl” is to be understood as meaning, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl-, tert-butyl-, pentyl-, 2-methylbutyl- or hexylsulfinyl group;

[0079] the term “(C₁-C₆)-alkylsulfonyl” is to be understood as meaning, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl-, tert-butyl-, pentyl-, 2-methylbutyl—or hexylsulfonyl group;

[0080] the terms “(C₁-C₆)-haloalkylsulfinyl” and “(C₁-C₆)-haloalkylsulfonyl” are to be understood as meaning (C₁-C₆)-alkylsulfinyl and -sulfonyl radicals having the meanings given above in which one or more, in the case of fluorine optionally also all, hydrogen atoms of the hydrocarbon moiety are replaced by halogen, in particular chlorine or fluorine;

[0081] the term “(C₁-C₆)-alkoxy” is to be understood as meaning an alkoxy group whose hydrocarbon radical has the meaning given under the term “(C₁-C₆)-alkyl”;

[0082] the term “(C₁-C₈)-alkylamino” is to be understood as meaning, for example, the methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, sec-butylamino, tert-butylamino, pentylamino or the hexylamino group;

[0083] the term “(C₁-C₆)-dialkylamino” is to be understood as meaning, for example, the dimethylamino, methylethylamino, diethylamino, dipropylamino, dibutylamino, dipentylamino or the dihexylamino group; but also cyclic systems, such as, for example, the pyrrolidino or piperidino group,

[0084] the term “(C₁-C₆)-haloalkoxy” is to be understood as meaning a haloalkoxy group whose halohydrocarbon radical has the meaning given under the term “(C₁-C₆)-haloalkyl”;

[0085] the term “aryl” is to be understood as meaning a carbocyclic aromatic radical having preferably 6 to 14, in particular 6 to 12, carbon atoms, such as phenyl or naphthyl, preferably phenyl;

[0086] the term “heterocyclyl” is to be understood as meaning a heteroaromatic or heteroaliphatic ring system, where “heteroaromatic ring system” is to be understood as meaning an aryl radical in which at least one CH group is replaced by N and/or at least two adjacent CH groups are replaced by S, NH or O, for example a thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3,4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo[b]thiophene, benzo[b]furan, indole, benzo[c]thiophene, benzo[c]furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,4,5-triazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine or 4H-quinolizine radical;

[0087] and the term “heteroaliphatic ring system” is to be understood as meaning a (C₃-C₈)-cycloalkyl radical in which at least one carbon unit is replaced by O, S or a group NR¹¹ and R¹¹ is hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy or aryl;

[0088] the term “arylthio” is to be understood as meaning, for example, the phenylthio group;

[0089] the term “aryloxy” is to be understood as meaning, for example, the phenoxy group;

[0090] the term “heterocyclyloxy” or “heterocyclylthio” is to be understood as meaning one of the heterocyclic radicals mentioned above which is attached via an oxygen or sulfur atom;

[0091] the term “(C₃-C₈)-cycloalkoxy” or “(C₃-C₈)-cycloalkylthio” is to be understood as meaning one of the (C₃-C₈)-cycloalkyl radicals listed above which is attached via an oxygen or sulfur atom;

[0092] the term “(C₃-C₈)-cycloalkoxycarbonyl” is to be understood as meaning, for example, the cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl or the cycloheptyloxycarbonyl group;

[0093] and the term “unsubstituted or substituted aryl, heterocyclyl, phenyl, etc.” is to be understood as meaning, preferably, substitution by one or more, preferably 1 to 3, in the case of halogen also up to the maximum number of, radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, thio, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₈)-cycloalkyl, (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylamino, (C₁-C₄)-haloalkylamino, formyl or (C₁-C₄)-alkanoyl.

[0094] The explanation given above applies correspondingly to homologs and radicals derived therefrom.

[0095] The present invention relates to the compounds of the formula (I) in the form of the free base or an acid addition salt. Acids which can be used for salt formation are, for example, inorganic acids, such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, or organic acids, such as formic acid, acetic acid, propionic acid, malonic acid, oxalic acid; fumaric acid, adipic acid, stearic acid, oleic acid, methanesulfonic acid, benzenesulfonic acid or toluenesulfonic acid.

[0096] In some cases, the compounds of the formula (I) contain one or more chiral carbon atoms or stereoisomers on double bonds. Enantiomers or diastereomers can therefore occur. The invention relates both to the pure isomers and to mixtures thereof. The mixtures of diastereomers can be separated into the components by customary methods, for example by selective crystallization from suitable solvents or by chromatography. Racemates can be separated into the enantiomers by customary methods, thus, for example, by salt formation with a chiral, enantiomerically pure acid, separation of the diastereomeric salts and liberation of the pure enantiomers by means of a base.

[0097] The compounds according to the invention are prepared by methods which are known per se from the literature, as described in standard works on organic synthesis, for example Houben-Weyl, Methoden der Organischen Chemie [Methods in Organic Chemistry], Georg-Thieme-Verlag, Stuttgart.

[0098] The preparation is carried out under reaction conditions which are known and suitable for the abovementioned reactions. Other variants which are known per se, but not illustrated here in greater detail, may also be used.

[0099] If desired, the starting materials may also be formed in situ, in such a way that they are not isolated from the reaction mixture but immediately reacted further to give the compounds of the formula (I).

[0100] The general chemistry of 1,3-oxazolines is described, for example, in Tetrahedron, 1994, 50, 2297-2360 and in Nachr. Chem. Tech. Lab. 1996, 44, 744-750.

[0101] The invention also provides a process for preparing compounds of the formula (I, G=3-isoxazinyl) by reacting 1,3-oxazolines, 1,3-thiazolines, pyrrolines and imidazolines of the formula (II) (see, for example, WO-A-96/22283) (suitably substituted by X_(n) and R¹ _(m)) with a halogenating agent to give compounds of the formula (III), and reacting these compounds with an olefin (IV) (suitably substituted by R⁵ _(t)), where initially an oxime of the formula (II),

[0102] in which

[0103] X and Z have the meanings given in formula (I)

[0104] is reacted with a halogenating agent, preferably a chlorinating agent, to give a compound of the formula (III)

[0105] in which

[0106] Hal is halogen, preferably Cl,

[0107] and then reacted further with an olefin of the formula (IV),

[0108] in which R⁵ and t have the meanings given above.

[0109] The invention also provides a process for preparing compounds of the formula (II) by reacting 1,3-oxazolines, 1,3-thiazolines, pyrrolines and imidazolines of the formula (V) (suitably substituted by X and R¹) with hydroxylamine or its salts, if appropriate in the presence of a base,

[0110] in which

[0111] X_(n) and Z have the meanings given in formula (I).

[0112] The invention also provides a process for preparing compounds of the formula (V) from 1,3-oxazolines, 1,3-thiazolines, pyrrolines and imidazolines of the formula (VI) (suitably substituted by X and R¹), where compounds of the formula (VI)

[0113] in which

[0114] Y¹ and Y² independently of one another are hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxycarbonyl or phenyl and

[0115] X_(n) and Z have the meanings given in formula (I)

[0116] are reacted with an oxidizing agent to give compounds of the formula (V).

[0117] Methods A to D are illustrated using the synthesis of different subgroups of compounds of the formula (I), (G=3-isoxazinyl) as an example:

[0118] The isoxazole ring is advantageously generated in the presence of a base, for example selected from the group of the alkali metal hydroxides, alkali metal carbonates, alkoxides and amines.

[0119] Using halogenating agents, oximes of the formula (II) are converted into the halooximes (III). Suitable halogenating agents are, for example, elemental halogen, hypohalites and N-haloimides:

[0120] Oximes of the formula (II) are prepared by reacting aldehydes of the formula (V) with hydroxylamine or hydroxylamine salts, if appropriate in the presence of a base:

[0121] Aldehydes of the formula (V) are generated by cleaving the olefins of the

[0122] formula (VI) using an oxidizing agent. Suitable oxidizing agents are, for example, ruthenium or osmium compounds in combination with a periodate, or ozone:

[0123] Some compounds of the formula (VI) have been described (WO-A-95/04726) or they can be prepared in a similar manner.

[0124] The invention also provides a process for preparing compounds of the formula (I) (G=5-isoxazinyl) by reacting 1,3-oxazolines, 1,3-thiazolines, pyrrolines and imidazolines of the formula (VII) (see, for example, WO-A 95/04726), suitably substituted by X_(n) and R¹ _(m), with a halooxime, where an olefin of the formula (VII)

[0125] in which

[0126] Z and R⁵ _(t) have the meanings given above, is reacted with a halooxime of the formula (VIII)

[0127] where R⁵ has the meanings given above.

[0128] Method E is illustrated using the synthesis of compounds of the formula (I) (G=3-isoxazinyl) as an example:

[0129] The isoxazole ring is generated in the presence of a base, selected, for example, from the group consisting of alkali metal hydroxides, alkali metal carbonates, alkoxides and amines.

[0130] Various esters and amides as radicals R⁵ can be prepared, for example, from acid derivatives. These, for their part, are obtainable, for example, by ester hydrolysis, for example

[0131] Suitable for use as hydrolyzing agents are, for example, aqueous alkali metal hydroxide solutions.

[0132] During the preparation of the amides or esters, the acid can be activated using, for example, a carboduimide, carbonylduimidazole or an inorganic acid chloride, for example thionyl chloride.

[0133] Various esters and amides as radical R⁵ can also be prepared, for example, from hydroxyl and amine derivatives. These, for their part, are obtainable, for example, by ester or amide hydrolysis, for example:

[0134] Suitable for use as hydrolyzing agents are, for example, aqueous alkali metal hydroxide solutions.

[0135] To prepare the amides or esters, the alcohol or the amine can be reacted, for example, with an activated acid, e.g. an acid chloride.

[0136] Collections of compounds of the formula (I) which can be synthesized by the abovementioned scheme may also be prepared in a parallel manner and this may be effected manually or in a semiautomated or fully automated manner. In this case, it is possible, for example, to automate the procedure of the reaction, the work-up or the purification of the products or of the intermediates. In total, this is to be understood as meaning a procedure as is described, for example, by S. H. DeWitt in “Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated synthesis”, Volume 1, Verlag Escom 1997, pages 69 to 77.

[0137] A number of commercially available apparatuses as are offered by, for example, Stem Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE, England or H+P Labortechnik GmbH, Bruckmannring 28, 85764 Oberschleiβheim, Germany, may be used for the parallel procedure of the reaction and work-up. For the parallel purification of compounds of the formula (I), or of intermediates obtained during the preparation, use may be made, inter alia, of chromatography apparatuses, for example those from ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA.

[0138] The apparatuses mentioned lead to a modular procedure in which the individual process steps are automated, but manual operations have to be performed between the process steps. This can be avoided by employing semiintegrated or fully integrated automation systems where the automation modules in question are operated by, for example, robots. Such automation systems can be obtained, for example, from Zymark Corporation, Zymark Center, Hopkinton, Mass. 01748, USA.

[0139] In addition to what has been described here, compounds of the formula (I) may be prepared in part or fully by solid-phase-supported methods. For this purpose, individual intermediate steps or all intermediate steps of the synthesis or of a synthesis adapted to suit the procedure in question are bound to a synthetic resin. Solid-phase-supported synthesis methods are described extensively in the specialist literature, for example Barry A. Bunin in “The Combinatorial Index”, Verlag Academic Press, 1998.

[0140] The use of solid-phase-supported synthesis methods permits a series of protocols which are known from the literature and which, in turn, can be performed manually or in an automated manner. For example, the “tea-bag method” (Houghten, U.S. Pat. No. 4,631,211; Houghten et al., Proc. Natl. Acad. Sci, 1985, 82, 5131-5135), in which products from IRORI, 11149 North Torrey Pines Road, La Jolla, Calif. 92037, USA, are employed, may be semiautomated. The automation of solid-phase-supported parallel syntheses is performed successfully, for example, by apparatuses from Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, Calif. 94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Germany.

[0141] The preparation according to the processes described herein yields compounds of the formula (I) in the form of substance collections which are referred to as libraries. The present invention also relates to libraries which comprise at least two compounds of the formula (I).

[0142] The compounds of the formula (I) are suitable for controlling animal pests, in particular insects, arachnids, helminths and molluscs, very especially preferably for controlling insects and arachnids, which are encountered in agriculture, in livestock breeding, in forests, in the protection of stored goods and materials and in the hygiene sector, and have good plant tolerance and favorable toxicity to warm-blooded species. They are active against normally sensitive and resistant species and against all or individual development stages. The abovementioned pests include:

[0143] From the order of the Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp. and Eutetranychus spp.

[0144] From the order of the Isopoda, for example, Oniscus asselus, Armadium vulgare and Porcellio scaber.

[0145] From the order of the Diplopoda, for example, Blaniulus guttulatus.

[0146] From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spp.

[0147] From the order of the Symphyla, for example, Scutigerella immaculata.

[0148] From the order of the Thysanura, for example, Lepisma saccharina.

[0149] From the order of the Collembola, for example, Onychiurus armatus.

[0150] From the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea madeira, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria.

[0151] From the order of the Isoptera, for example, Reticulitermes spp.

[0152] From the order of the Anoplura, for example, Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.

[0153] From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp.

[0154] From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci.

[0155] From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.

[0156] From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.

[0157] From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima and Tortrix viridana.

[0158] From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylloides chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonumus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrynchus assimilis, Hypera postica, Dermestes spp., Trogoderma, Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon soistitialis and Costelytra zealandica.

[0159] From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

[0160] From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa.

[0161] From the order of the Siphonaptera, for example, Xenopsylla cheopsis and Ceratophyllus spp.

[0162] From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans.

[0163] From the class of helminths, for example, Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis, as well as Fasciola.

[0164] From the class of the Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp. and Oncomelania spp.

[0165] From the class of Bivalva, for example, Dreissena spp.

[0166] The phytoparasitic nematodes which can be controlled according to the invention include, for example, the root-parasitic soil nematodes, such as, for example, those of the genera Meloidogyne (root gall nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida and Heterodera trifolii) and of the genera Radopholus, such as Radopholus similis, Pratylenchus, such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus, Tylenchulus, such as Tylenchulus semipenetrans, Tylenchorhynchus, such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni, Rotylenchus, such as Rotylencus robustus, Heliocotylenchus, such as Heliocotylenchus multicinctus, Belonoaimus, such as Belonoaimus longicaudatus, Longidorus, such as Longidorus elongatus, Trichodorus, such as Trichodorus primitivus and Xiphinema, such as Xiphinema index.

[0167] The nematode genera Ditylenchus (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes, such as Aphelenchoides ritzemabosi) and Anguina (blossom nematodes, such as Anguina tritici) can furthermore be controlled with the compounds according to the invention.

[0168] The invention also relates to compositions, for example crop protection compositions, preferably insecticidal, acaricidal, ixodicidal, nematicidal, molluscidal or fungicidal, particularly preferably insecticidal and acaricidal compositions, which comprise one or more compounds of the formula (I) in addition to suitable formulation auxiliaries.

[0169] In general, the compositions according to the invention comprise from 1 to 95% by weight of the active compounds of the formula (I).

[0170] For preparing the compositions according to the invention, the active compound and the other additives are combined and formulated as a suitable use form. They can be formulated in various ways, depending on how this is predetermined by the biological and/or chemico-physical parameters. Suitable formulation possibilities are therefore:

[0171] Wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions, sprayable solutions, oil- or water-based dispersions (SC), suspoemulsions (SE), dusting powders (DP), seed dressings, granules in the form of microgranules, sprayed granules, absorption granules and adsorption granules, water-dispersible granules (WG), ULV formulations, microcapsules, waxes or baits.

[0172] These individual types of formulation are known in principle and are described, for example, in: Winnacker-Küchler, “Chemische Technologie” [Phemical Technology], Volume 7, C. Hanser Verlag Munich, 4th Edition 1986; van Falkenberg, “Pesticides Formulations”, Marcel Dekker N.Y., 2nd Edition 1972-73; K. Martens, “Spray Drying Handbook”, 3rd Edition 1979, G. Goodwin Ltd. London.

[0173] The necessary formulation auxiliaries, such as inert materials, surfactants, solvents and further additives, are likewise known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Edition, Darland Books, Caldwell N.J.; H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd Edition, J. Wiley & Sons, N.Y.; Marsden, “Solvents Guide”, 2nd Edition, Interscience, N.Y. 1950; McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1967; Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hanser Verlag Munich, 4th Edition 1986.

[0174] Combinations with other substances having a pesticidal action, fertilizers and/or growth regulators can be prepared on the basis of these formulations, for example in the form of a ready-to-use formulation or as a tank mix. Wettable powders are preparations which are uniformly dispersible in water and which, alongside the active compound, and in addition to a diluent or inert substance, also comprise wetting agents, for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols or alkyl- or alkylphenolsulfonates, and dispersing agents, for example sodium ligninsulfonate or sodium 2,2′-dinaphthylmethane-6,6′-disulfonate.

[0175] Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons, with the addition of one or more emulsifiers. Emulsifiers which can be used are, for example: calcium alkylaryl-sulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

[0176] Dusting powders are obtained by grinding the active compound with finely divided solid substances, for example talc, naturally occurring clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. Granules can be prepared either by spraying the active compound onto granular inert material capable of adsorption or by applying active compound concentrates to the surface of carrier substances, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils. Suitable active compounds can also be granulated in the manner customary for the preparation of fertilizer granules—if desired as a mixture with fertilizers.

[0177] In wettable powders, the active compound concentration is for example about 10 to 90% by weight, the remainder to make up 100% by weight comprising customary formulation constituents. In emulsifiable concentrates, the active compound concentration can be about 5 to 80% by weight. Dust-like formulations usually comprise 5 to 20% by weight of active compound, and sprayable solutions about 2 to 20% by weight. In granules, the content of active compound partly depends on whether the active compound is present in liquid or solid form and what granulating auxiliaries, fillers and the like are used.

[0178] In addition, the active compound formulations mentioned comprise, if appropriate, the particular customary tackifiers, wetting agents, dispersing agents, emulsifiers, penetration agents, solvents, fillers or carrier substances.

[0179] For use, the concentrates in the commercially available form are diluted in the customary manner, if appropriate, for example by means of water in the case of wettable powders, emulsifiable concentrates, dispersions and in some cases also microgranules. Dust-like and granular formulations as well as sprayable solutions are usually not diluted further with additional inert substances before use.

[0180] The required amount applied varies with the external conditions, such as temperature or humidity. It can vary within wide limits, for example between 0.0005 and 10.0 kg/ha or more of active substance, but is preferably between 0.001 and 5 kg/ha.

[0181] The active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations (see the above mentioned compositions) as mixtures with other active compounds, such as insecticides, attractants, sterilizing agents, acaricides, nematicides, fungicides, molluscides, growth-regulating substances or herbicides. The pesticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds and substances produced by microorganisms.

[0182] Preferred partners for the mixtures are:

[0183] 1. from the group of phosphorus compounds

[0184] acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos (F-67825), chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, demeton, demeton-S-methyl, demeton-S-methyl sulfone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitriothion, fensulfothion, fenthion, fonofos, formothion, fosthiazate (ASC-66824), heptenophos, isazophos, isothioate, isoxathion, malathion, methacrifos, methamidophos, methidathion, salithion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosfolan, phosphocarb (BAS-301), phosmet, phosphamidon, phoxim, pirimiphos, primiphos-ethyl, pirimiphos-methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, suiprofos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thiometon, triazophos, trichlorphon, vamidothion;

[0185] 2. from the group of carbamates

[0186] alanycarb (OK-135), aldicarb, 2-sec-butylphenyl methylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb, benfuracarb, ethiofencarb, furathiocarb, HCN-801, isoprocarb, methomyl, 5-methyl-m-cumenyl butyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, 1-methylthio(ethylideneamino) N-methyl-N-(morpholinothio)carbamate (UC 51717), triazamate;

[0187] 3. from the group of carboxylic acid esters

[0188] acrinathrin, allethrin, alphametrin, 5-benzyl-3-furylmethyl (E)-(1R)-cis-2,2-di-methyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, beta-cyfluthrin, beta-cypermethrin, cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, bifenthrin, (RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methyl (1RS)-trans-3-(4-tert-butylphenyl)-2,2-dimethylcyclopropanecarboxylate (NCI 85193), cycloprothrin, cyfluthrin, cyhalothrin, cythithrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin (S-41311), lambda-cyhalothrin, permethrin, pheothrin ((R) isomer), prallethrin, pyrethrins (natural products), resmethrin, tefluthrin, tetramethrin, theta-cypermethrin (TD-2344), tralomethrin, transfluthrin and zeta-cypermethrin (F-56701);

[0189] 4 from the group of amidines

[0190] amitraz, chlordimeform;

[0191] 5. from the group of tin compounds

[0192] cyhexatin, fenbutatin oxide;

[0193] 6. others

[0194] abamectin, ABG-9008, acetamiprid, Anagrapha falcitera, AKD-1022, AKD-3059, ANS-118, Bacillus thuringiensis, Beauveria bassianea, bensultap, bifenazate (D-2341), binapacryl, BJL-932, bromopropylate, BTG-504, BTG-505, buprofezin, camphechlor, cartap, chlorobenzilate, chlorfenapyr, chlorfluazuron, 2-(4-chlorophenyl)-4,5-diphenylthiophene (UBI-T 930), chlorfentezine, chromafenozide (ANS-118), CG-216, CG-217, CG-234, A-184699, 2-naphthylmethyl cyclopropanecarboxylate (Ro12-0470), cyromazin, diacloden (thiamethoxam), diafenthiuron, N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propyloxy)phenyl)carbamoyl)-2-chlorobenzocarboxamide acid ethyl ester, DDT, dicofol, diflubenzuron, N-(2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene)-2,4-xylidine, dinobuton, dinocap, diofenolan, DPX-062, emamectin-benzoate (MK-244), endosulfan, ethiprole (sulfethiprole), ethofenprox, etoxazole (YI-5301), fenazaquin, fenoxycarb, fipronil, fluazuron, flumite (flufenzine, SZI-121), 2-fluoro-5-(4-(4-ethoxyphenyl)-4-methyl-1-pentyl)diphenyl ether (MTI 800), granulosis and nuclear polyhedrosis viruses, fenpyroximate, fenthiocarb, flubenzimine, flucycloxuron, flufenoxuron, flufenprox (ICI-A5683), fluproxyfen, gamma-HCH, halofenozide (RH-0345), halofenprox (MTI-732), hexaflumuron (DE-473), hexythiazox, HOI-9004, hydramethylnon (AC 217300), IKI 220, imidacloprid, indoxacarb (DPX-MP062), kanemite (AKD-2023), M-020, MTI-446, ivermectin, lufenuron, M-020, methoxyfenozide (Intrepid, RH-2485), milbemectin, NC-196, neemgard, nitenpyram (TI-304), 2-nitromethyl-4,5-dihydro-6H-thiazine (DS 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651), 2-nitromethylene-1,2-thiazinan-3-ylcarbamaldehyde (WL 108477), pyriproxyfen (S-71639), NC-196, NC-1111, NNI-9768, novaluron (MCW-275), OK-9701, OK-9601, OK-9602, propargite, pymethrozine, pyridaben, pyrimidifen (SU-8801), RH-0345, RH-2485, RYI-210, S-1283, S-1833, SB7242, SI-8601, silafluofen, silomadine (CG-177), spinosad, SU-9118, tebufenozide, tebufenpyrad (MK-239), teflubenzuron, tetradifon, tetrasul, thiacloprid, thiocyclam, TI-435, tolfenpyrad (OMI-88), triazamate (RH-7988), triflumuron, verbutin, vertalec (Mykotal), YI-5301.

[0195] The active compound content of the use forms prepared from the commercially available formulations can be from 0.00000001 to 95% by weight of active compound, preferably between 0.00001 and 1% by weight. The active compounds are used in a customary manner appropriate for the use forms.

[0196] The invention also provides a method for controlling harmful insects, Acarina, molluscs and/or nematodes, in which an effective amount of a compound according to the invention or a composition according to the invention is applied to these organisms or the plants, areas or substrates infested with them.

[0197] The invention also provides the use of a compound according to the invention or a composition according to the invention for controlling harmful insects, Acarina, molluscs and/or nematodes.

[0198] The active substances according to the invention are also suitable for the field of veterinary medicine, preferably for controlling endo- and ectoparasites, and for the field of animal husbandry.

[0199] The active substances according to the invention can preferably be applied in a known manner, such as by oral application in the form of, for example, tablets, capsules, potions or granules, by dermal application in the form of, for example, dipping, spraying, pouring-on and spotting-on and dusting, and also by parenteral application in the form of, for example, injection.

[0200] The compounds of the formula (I) according to the invention can accordingly also be employed particularly advantageously in livestock husbandry (for example cattle, sheep, pigs and poultry such as chickens, geese etc.). In a preferred embodiment of the invention, the novel compounds, if appropriate in suitable formulations (cf. above) and if appropriate with the drinking water or feed, are administered orally to the animals. Since excretion in the feces occurs in an effective fashion, the development of insects in the animal feces can be prevented very simply in this fashion. The dosages and formulations suitable in each case, in particular, depend on the type and developmental stage of the productive animals and also on the severity of infestation and can easily be determined and fixed by conventional methods. In the case of cattle, the compounds can be employed, for example, in dosages of 0.01 to 1 mg/kg of body weight.

[0201] Accordingly, the invention also provides the use of a compound of the formula (I) or one of the abovementioned compositions for preparing a veterinary medicament.

[0202] In addition, the compounds according to the invention are also suitable for use in industrial fields, for example as wood preservative, as preservative in paints, in cooling lubricants for metal working or as preservative in drilling and cutting oils. Compounds of the formula (I) in their commercially available formulations can be used either alone or in combination with other fungicides known from the literature.

[0203] Examples of fungicides which are known from the literature and which can be combined in accordance with the invention with the compounds of the formula (I) are the following products:

[0204] aldimorph, andoprim, anilazine, BAS 480F, BAS 450F, benalaxyl, benodanil, benomyl, binapacryl, bitertanol, bromuconazole, buthiobate, captafol, captan, carbendazim, carboxin, CGA 173506, cyprofuram, dichlofluanid, dichlomezin, diclobutrazol, diethofencarb, difenconazole (CGA 169374), difluconazole, dimethirimol, dimethomorph, diniconazole, dinocap, dithianon, dodemorph, dodine, edifenfos, ethirimol, etridiazol, fenarimol, fenfuram, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferimzone (TF164), fluazinam, fluobenzimine, fluquinconazole, fluorimide, flusilazole, flutolanil, flutriafol, folpet, fosetyl-aluminum, fuberidazole, fulsulfamide (MT-F 651), furalaxyl, furconazole, furmecyclox, guazatine, hexaconazole, ICI A5504, imazalil, imibenconazole, iprobenfos, iprodione, isoprothiolane, KNF 317, copper compounds such as copper oxychloride, oxine-copper, copper oxide, mancozeb, maneb, mepanipyrim (KIF 3535), metconazole, mepronil, metalaxyl, methasulfocarb, methfuroxam, MON 24000, myclobutanil, nabam, nitrothalidopropyl, nuarimol, ofurace, oxadixyl, oxycarboxin, penconazole, pencycuron, PP 969, probenazole, propineb, prochloraz, procymidon, propamocarb, propiconazole, prothiocarb, pyracarbolid, pyrazophos, pyrifenox, pyroquilon, rabenzazole, RH7592, sulfur, tebuconazole, TF 167, thiabendazole, thicyofen, thiofanate-methyl, thiram, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, tricyclazole, tridemorph, triflumizole, triforine, validamycin, vinchlozolin, XRD 563, zineb, sodium dodecylsulfonate, sodium dodecyl sulfate, sodium C13/C15-alcohol ether sulfonate, sodium cetostearyl phosphate ester, sodium dioctylsulfosuccinate, sodium isopropyinaphthalenesulfonate, sodium methylenebisnaphthalenesulfonate, cetyltrimethylammonium chloride, salts of long-chain primary, secondary or tertiary amines, alkylpropyleneamines, laurylpyrimidinium bromide, ethoxylated quaternized fatty amines, alkyldimethylbenzylammonium chloride and 1-hydroxylethyl-2-alkylimidazoline.

[0205] The abovementioned components are known active substances, many of which are described in C. D. S. Tomlin, S. B. Walker, The Pesticide Manual, 12th Edition, British Crop Protection Council, Farnham 2000.

[0206] The invention also provides seed, comprising or coated with an effective amount of a compound according to the invention or of a composition according to the invention.

[0207] The compounds of the formula (I) can also be employed for controlling harmful organisms in crops of known or genetically engineered plants yet to be developed. As a rule, the transgenic plants are distinguished by particular advantageous properties, for example by resistances to certain crop protection agents, resistances to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other particular properties relate, for example, to the harvested material with regard to quantity, quality, storage properties, composition and specific constituents. Thus, transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid spectrum of the harvested material, are known.

[0208] The use in economically important transgenic crops of useful plants and ornamentals, for example, cereals such as wheat, barley, rye, oats, millet and sorghum, rice, cassava and maize or else crops of sugar beet, cotton, soya, oilseed rape, potatoes, tomatoes, peas and other vegetables is preferred.

[0209] When being use in transgenic crops, in particular those in which the plants express an insecticide, effects are frequently found (in addition to the pesticidal effects which can be observed in other crops) which are specific to application in the transgenic crop in question, for example an altered or specifically widened spectrum of pests which can be controlled, or altered application rates which can be used for application.

[0210] The invention therefore also provides the use of compounds of the formula (I) for controlling harmful organisms in transgenic crop plants.

[0211] The use according to the invention of compounds of the formula (I) or compositions comprising them, for example an insecticide, acaricide, molluscide or nematicide, includes the case where the compound of the formula (I) or its salt is formed from a precursory substance only after application, for example in the insect, in a plant or in the soil.

[0212] The contents of German patent application 101 14 597.7, whose priority is claimed by the present application, and the contents of the appended summary are hereby incorporated herein by reference; they are . . . .

[0213] The examples which follow serve to illustrate the invention without restricting it thereto.

A. PREPARATION EXAMPLES

[0214] 3-Arylisoxazolines

[0215] Intermediate I2: 2-(2,6-difluorophenyl)-4-(4-(2-phenylethenyl)phenyl)oxazoline

[0216] 2-(2,6-Difluorophenyl)-4-(4-bromophenyl)oxazoline (33.8 g, 0.1 mol) and styrene (22.9 ml, 0.2 mol) in 300 ml of DMF were heated at reflux with sodium carbonate (11.66 g, 0.11 mol), tris(2,4-di-tert-butylphenyl)phosphite (6.47 g, 10 mmol) and palladium acetate (0.45 g, 2 mmol) for 20 h. Following extractive work-up with ethyl acetate, the residue was triturated with heptane/dichloromethane (1:1). This gave 27 g of crystals, m.p. 141° C.

[0217] Intermediate I2: 2-(2,6-difluorophenyl)-4-(4-formylphenyl)oxazoline

[0218] At 0° C., 2-(2,6-difluorophenyl)-4-(4-(2-phenylethenyl)phenyl)oxazoline (7.22 g, 20 mmol) and sodium metaperiodate (8.55 g, 20 mmol) were suspended in acetonitrile/acetone/water (1:1:1, 180 ml), and a catalytic amount of ruthenium trichloride hydrate was added. Following extractive work-up with ethyl acetate and column chromatography, 5.6 g of the aldehyde were obtained as a viscous oil.

[0219] Intermediate I3: 2-(2,6-difluorophenyl)-4-(4-(hydroxyiminomethyl)phenyl)oxazoline

[0220] At room temperature, 2-(2,6-difluorophenyl)-4-(4-formylphenyl)oxazoline (5.6 g), hydroxylamine hydrochloride (1.53 g, 1.1 equivalents) and sodium acetate (4.9 g, 3 equivalents) were stirred in 50 ml of ethanol for 24 h. Following extractive work-up with ethyl acetate and column chromatography, 4.2 g of crystals were obtained, m.p. 159° C.

[0221] 2-(2,6-Difluorophenyl)-4-(4-(5-tert-butylisoxazolin-3-yl)phenyl)oxazoline (Ex. No. 9)

[0222] At 50° C., 2-(2,6-difluorophenyl)-4-(4-(hydroxyiminomethyl)phenyl)oxazoline (40 mg, 0.13 mmol) and N-chlorosuccinimide (19 mg, 1.1 equivalents) in 2 ml of DMF were heated for 4 h. After cooling to room temperature, 3,3-dimethylbutene (33 mg, 0.4 mmol) and triethylamine (41 mg, 0.4 mmol) were added. After 16 h of stirring, the mixture was worked up by extraction with ethyl acetate and the residue was purified by column chromatography. This gave 19 mg of product.

[0223] 2-(2,6-Difluorophenyl)-4-(4-(5-trifluoromethylisoxazolin-3-yl)phenyl)oxazoline (Ex. No. 43)

[0224] At 50° C., 2-(2,6-difluorophenyl)-4-(4-(hydroxyiminomethyl)phenyl)oxazoline (40 mg, 00.13 mmol) and N-chlorosuccinimide (19 mg, 1.1 equivalents) in 2 ml of DMF were heated for 4 h. After cooling to room temperature, 2 ml of a DMF solution saturated with 3,3,3-trifluoropropene, and triethylamine (41 mg, 0.4 mmol) were added. After 16 h of stirring, the mixture was worked up by extraction with ethyl acetate and the residue was purified by column chromatography. This gave 37 mg of product.

[0225] 2-(2,6-Difluorophenyl)-4-(4-(5-(trifluoroacetamidomethyl)isoxazolin-3-yl) phenyl)oxazoline (Ex. No.115)

[0226] At 50° C., 2-(2,6-difluorophenyl)-4-(4-(hydroxyiminomethyl)phenyl)oxazoline (1.2 g, 4 mmol) and N-chlorosuccinimide (560 mg, 1.05 equivalents) in 6 ml of DMF were heated for 4 h. After cooling to room temperature, N-allyltrifluoroacetamide (2.75 g, 3 equivalents) and triethylamine (1.66 ml, 3 equivalents) were added. After 16 h of stirring, the mixture was worked up by extraction with ethyl acetate and the residue was purified by column chromatography. This gave 920 mg of product.

[0227] 2-(2,6-Difluorophenyl)-4-(4-(5-(propionylaminomethyl)isoxazolin-3-yl)phenyl)-oxazoline (Ex. No. 116)

[0228] 2-(2,6-Difluorophenyl)-4-(4-(5-(trifluoroacetamidomethyl)isoxazolin-3-yl)phenyl)-oxazoline (43 mg) in 2 ml of methanol was admixed with 0.5 ml of 2N aqueous sodium hydroxide solution, and the mixture was stirred for 16 h. Following extractive work-up with dichloromethane, triethylamine (0.05 ml) and propionyl chloride (50 mg) were added at 0° C. to the crude amine in 2 ml of dichlromethane. After 2 h of stirring, the mixture was worked up by extraction with ethyl acetate and the residue was purified by column chromatography. This gave 40 mg of product.

[0229] 5-Arylisoxazolines

[0230] Intermediate 14: 2-(2,6-difluorophenyl)-4-(4-ethenylphenyl)oxazoline

[0231] In an autoclave, 2-(2,6-difluorophenyl)-4-(4-bromophenyl)oxazoline (6.0 g, 18 mmol), sodium carbonate (2.9 g, 21 mmol), tris(2,4-di-tert-butylphenyl) phosphite (1.2 g, 1.8 mmol) and palladium acetate (64 mg, 2% equivalents) in 100 ml of DMF were heated under 20 bar of ethylene at 150° C. for 44 h. Extractive work-up with ethyl acetate and column chromatography gave 3.75 g of crystals, m.p. 76° C.

[0232] 2-(2,6-Difluorophenyl)-4-(4-(3-methylisoxazolin-5-yl)phenyl)oxazoline (Ex. No. 566)

[0233] At room temperature, acetaldoxime (30 mg, 0.5 mmol) and N-chlorosuccinimide (67 mg, 1 equivalent) in 3 ml of DMF were stirred for 3 h. 2-(2,6-Difluorophenyl)-4-(4-ethenylphenyl)oxazoline (43 mg, 0.15 mmol) and triethylamine (46 mg, 0.45 mmol) were then added, and the mixture was stirred for 16 h. Extractive work-up with ethyl acetate and column chromatography gave 32 mg of product.

[0234] 2-(2,6-Difluorophenyl)-4-(4-(3-tert-butylisoxazolin-5-yl)phenyl)oxazoline (Ex. No. 573)

[0235] At room temperature, pivalaldehyde oxime (51 mg, 0.5 mmol) and N-chloro-succinimide (67 mg, 1 equivalent) in 3 ml of DMF were stirred for 3 h. 2-(2,6-Difluorophenyl)-4-(4-ethenylphenyl)oxazoline (43 mg, 0.15 mmol) and triethylamine (46 mg, 0.45 mmol) were then added, and the mixture was stirred for 16 h. Extractive work-up with ethyl acetate and column chromatography gave 30 mg of product.

[0236] 2-(2,6-Difluorophenyl)-4-(4-(3-ethoxycarbonylisoxazolin-5-yl)phenyl)oxazoline (Ex. No. 614)

[0237] At 0° C., triethylamine (0.33 ml, 1.05 equivalents) was added to 2-(2,6-difluoro-phenyl)-4-(4-ethenylphenyl) oxazoline (570 mg, 2 mmol) and ethyl 2-chloro-2-hydroxyimino acetate (320 mg, 1.05 equivalents) in 10 ml of dichloroethane, and the mixture was stirred at room temperature for 16 h. Extractive work-up with ethyl acetate and column chromatography gave 420 mg of product.

[0238] 2-(2,6-Difluorophenyl)-4-(4-(3-(2,2,2-trifluoroethylaminocarbonyl)isoxazolin-5-yl) phenyl)oxazoline (Ex. No. 628)

[0239] 2-(2,6-Difluorophenyl)-4-(4-(3-ethoxycarbonylisoxazolin-5-yl)phenyl)oxazoline (769 mg, 1.9 mmol) in 20 ml of ethanol and 6.5 ml of 2N aqueous sodium hydroxide solution was stirred at room temperature for 3 h. The mixture was acidified with 2N hydrochloric acid and then worked up by extraction with dichloromethane. This gave 715 mg of crude acid which could be directly employed further.

[0240] 47 mg (0.13 mmol) of the crude acid in 2 ml of DMF were admixed with hydroxybenzotriazole (18 mg, 1 equivalent) and N-ethyl-N′-(3-dimethylamino-propyl)carbodiimide (25 mg, 1 equivalent). Ethyldiisopropylamine (17 mg, 1 equivalent) in 1 ml of THF and 2,2,2-trifluoroethylamine (0.015 ml) in 1 ml of THF were then added. The mixture was stirred at 50° C. for 16 h, and then worked up by extraction with ethyl acetate and column chromatography, giving 41 mg of product.

B. CHEMICAL EXAMPLES (TABLES 1-4)

[0241] TABLE 1 Oxazolines of the formula (I), Z = 0, G = 3-isoxazolinyl

Ex. Physical No. X¹ X² R′ R″ data 1 F F H H NMR 2 F F H CH₃ NMR 3 ″ ″ ″ C₂H₅ 4 ″ ″ ″ n-C₃H₇ 5 ″ ″ ″ i-C₃H₇ NMR 6 ″ ″ ″ n-C₄H₉ 7 ″ ″ ″ i-C₄H₉ 8 ″ ″ ″ s-C₄H₉ 9 ″ ″ ″ t-C₄H₉ NMR 10 ″ ″ ″ n-C₆H₁₃ NMR 11 ″ ″ ″ CH₂t-Bu NMR 12 ″ ″ ″ CH₂Cl NMR 13 ″ ″ ″ CH₂Br NMR 14 F F CH₃ CH₃ 15 ″ ″ ″ C₂H₅ 16 ″ ″ ″ n-C₃H₇ 17 ″ ″ ″ i-C₃H₇ 18 ″ ″ ″ s-C₄H₉ NMR 19 ″ ″ ″ i-C₄H₉ NMR 20 ″ ″ ″ t-C₄H₉ NMR 21 ″ ″ ″ n-C₆H₁₃ 22 ″ ″ ″ CH₂t-Bu NMR 23 ″ ″ ″ CH₂Cl NMR 24 F F H OCH₃ 25 ″ ″ ″ OC₂H₅ 26 ″ ″ ″ O-n-C₃H₇ 27 ″ ″ ″ O-n-C₄H₉ 28 ″ ″ ″ O-i-C₄H₉ NMR 29 ″ ″ ″ CN NMR 30 ″ ″ ″ CH₂CN NMR 31 ″ ″ ″ CH₂OCH₃ 32 ″ ″ ″ CH₂OC₂H₅ NMR 33 ″ ″ ″ CH₂O-n-C₃H₇ NMR 34 ″ ″ ″ CH₂O-i-C₃H₇ 35 ″ ″ ″ CH₂O-n-C₄H₉ NMR 36 ″ ″ ″ CH₂O-i-C₄H₉ 37 ″ ″ ″ CH₂O-s-C₄H₉ 38 ″ ″ ″ CH₂O-t-C₄H₉ 39 ″ ″ ″ CH₂OCF₂CF₂H NMR 40 ″ ″ ″ CH₂OCH₂CF₃ NMR 41 ″ ″ ″ CH₂O-phenyl NMR 42 ″ ″ ″ CH₂O-2-pyridyl NMR 43 ″ ″ ″ CF₃ NMR 44 ″ ″ ″ C₂H₅ 45 ″ ″ ″ n-C₃F₇ NMR 46 ″ ″ ″ n-C₄F₉ NMR 47 ″ ″ ″ n-C₅F₁₁ 48 ″ ″ ″ n-C₆F₁₃ NMR 49 ″ ″ ″ phenyl NMR 50 ″ ″ ″ 2-F-phenyl NMR 51 ″ ″ ″ 3-F-phenyl NMR 52 ″ ″ ″ 4-F-phenyl NMR 53 ″ ″ ″ 2-Cl-phenyl NMR 54 ″ ″ ″ 3-Cl-phenyl 55 ″ ″ ″ 4-Cl-phenyl NMR 56 ″ ″ ″ 2,4-Cl₂-phenyl 57 ″ ″ ″ 3,4-Cl₂-phenyl 58 ″ ″ ″ 2,6-Cl₂-phenyl NMR 59 ″ ″ ″ 4-Br-phenyl NMR 60 ″ ″ ″ 2-CF₃-phenyl NMR 61 ″ ″ ″ 3-CF₃-phenyl 62 ″ ″ ″ 3,5-(CF₃)₂-phenyl NMR 63 ″ ″ ″ 4-CF₃-phenyl NMR 64 ″ ″ ″ 2-CH₃-phenyl NMR 65 ″ ″ ″ 4-CH₃-phenyl NMR 66 ″ ″ ″ 2,4-(CH₃)₂-phenyl NMR 67 ″ ″ ″ 2,6-(CH₃)₂-phenyl 68 ″ ″ ″ 2,4,6-(CH₃)₃-phenyl NMR 69 ″ ″ ″ 2-CH₃O-phenyl 70 ″ ″ ″ 4-CH₃O-phenyl NMR 71 ″ ″ ″ 4-C₂H₅O-phenyl 72 ″ ″ ″ 4-CF₃O-phenyl NMR 73 ″ ″ ″ 4-CN-phenyl NMR 74 ″ ″ ″ 4-t-Bu-phenyl NMR 75 ″ ″ ″ 4-NO₂-phenyl 76 ″ ″ ″ CH₂phenyl NMR 77 ″ ″ ″ CH₂(4-F-phenyl) 78 ″ ″ ″ C₂H₄Br NMR 79 ″ ″ ″ CH₂SCH₃ NMR 80 ″ ″ ″ CH₂SOCH₃ 81 ″ ″ ″ CH₂SO₂CH₃ 82 ″ ″ ″ CH₂SC₂H₅ 83 ″ ″ ″ CH₂S-n-C₃H₇ 84 ″ ″ ″ COOCH₃ NMR 85 ″ ″ ″ COOC₂H₅ 86 ″ ″ ″ COOCH₂CF₃ NMR 87 ″ ″ ″ COOC₂H₄CF₃ NMR 88 ″ ″ ″ C₂F₄Br NMR 89 ″ ″ ″ CONHCH₃ 90 ″ ″ ″ CONHC₂H₅ NMR 91 ″ ″ ″ CON(CH₃)₂ NMR 92 ″ ″ ″ CON(C₂H₅)₂ NMR 93 ″ ″ ″ CONH(n-C₃H₇) NMR 94 ″ ″ ″ CONHCH₂C₂F₅ NMR 95 ″ ″ ″ CONHCH₂C₂H₃ NMR 96 ″ ″ ″ CONH-t-C₄H₉ NMR 97 ″ ″ ″ CONH-n-C₅H₉ NMR 98 ″ ″ ″ CONHC₃H₆OCH₃ NMR 99 ″ ″ ″ CONHCH₂C₃F₇ NMR 100 ″ ″ ″ CONHCH₂-(2-tetrahydrofuranyl) NMR 101 ″ ″ ″ CONH-phenyl 102 ″ ″ ″ CONH(4-F-phenyl) 103 ″ ″ ″ CONH(4-CF₃-phenyl) NMR 104 ″ ″ ″ CONCH₃(phenyl) 105 ″ ″ ″ CONCH₃(4-F-phenyl) 106 ″ ″ ″ CONH(4-Cl-phenyl) 107 ″ ″ ″ CONHC₂H₄(1-piperidinyl) NMR 108 ″ ″ ″ CONHCH₂CF₃ NMR 109 ″ ″ ″ CONHCH₂phenyl 110 ″ ″ ″ CONHCH₂(2,6-F₂-phenyl) NMR 111 ″ ″ ″ CONHCH₂(4-F-phenyl) 112 ″ ″ ″ CONHCH₂(4-CF₃-phenyl) 113 ″ ″ ″ CONHCH₂(3-CF₃-phenyl) NMR 114 ″ ″ ″ CH₂NHCOCH₃ NMR 115 ″ ″ ″ CH₂NHCOCF₃ NMR 116 ″ ″ ″ CH₂NHCOC₂H₅ NMR 117 ″ ″ ″ CH₂NHCOC₂H₅ NMR 118 ″ ″ ″ CH₂NHCO-n-C₃H₇ 119 ″ ″ ″ CH₂NHCO-i-C₃H₇ 120 ″ ″ ″ CH₂NHCO-n-C₃H₇ NMR 121 ″ ″ ″ CH₂NHCOC₂H₄CF₃ NMR 122 ″ ″ ″ CH₂NHCO-t-C₄H₉ 123 ″ ″ ″ CH₂NHCOphenyl 124 ″ ″ ″ CH₂NHCO(4-Cl-phenyl) NMR 125 ″ ″ ″ CH₂NHCO)2-Cl-5-pyridyl) NMR 126 F H H CH₃ 127 ″ ″ ″ C₂H₅ 128 ″ ″ ″ n-C₃H₇ 129 ″ ″ ″ i-C₃H₇ 130 ″ ″ ″ n-C₄H₉ 131 ″ ″ ″ i-C₄H₉ 132 ″ ″ ″ s-C₄H₉ 133 ″ ″ ″ t-C₄H₉ 134 ″ ″ ″ n-C₆H₁₃ 135 ″ ″ ″ CH₂-t-Bu 136 ″ ″ ″ CF₃ 137 ″ ″ ″ C₂H₅ 138 ″ ″ ″ n-C₃H₇ 139 ″ ″ ″ n-C₄F₉ NMR 140 ″ ″ ″ n-C₅F₁₁ 141 ″ ″ ″ n-C₆F₁₃ NMR 142 ″ ″ ″ phenyl 143 ″ ″ ″ 2-F-phenyl 144 ″ ″ ″ 3-F-phenyl 145 ″ ″ ″ 4-F-phenyl 146 ″ ″ ″ 2-Cl-phenyl 147 ″ ″ ″ 3-Cl-phenyl 148 ″ ″ ″ 4-Cl-phenyl NMR 149 ″ ″ ″ 2,4-Cl₂-phenyl 150 ″ ″ ″ 3,4-Cl₂-phenyl 151 ″ ″ ″ 2,5-Cl₂-phenyl 152 ″ ″ ″ 2,6-Cl₂-phenyl 153 ″ ″ ″ 2,CF₃-phenyl 154 ″ ″ ″ 3,CF₃-phenyl 155 ″ ″ ″ 3,5-(CF₃)₂-phenyl 156 ″ ″ ″ 4-CF₃-phenyl 157 ″ ″ ″ 2-CH₃-phenyl 158 ″ ″ ″ 4-CH₃-phenyl 159 ″ ″ ″ 2,4-(CH₃)₂-phenyl 160 ″ ″ ″ 2,6-(CH₃)₂-phenyl 161 ″ ″ ″ 2,4,6-(CH₃)₃-phenyl 162 ″ ″ ″ 2-CH₃O-phenyl 163 ″ ″ ″ 4-CH₃O-phenyl 164 ″ ″ ″ 4-C₂H₅O-phenyl 165 ″ ″ ″ 4-CF₃O-phenyl 166 ″ ″ ″ 4-CN-phenyl 167 ″ ″ ″ 3-NO₂-phenyl 168 ″ ″ ″ 4-NO₂-phenyl 169 F Cl H CH₃ 170 ″ ″ ″ C₂H₅ 171 ″ ″ ″ n-C₃H₇ 172 ″ ″ ″ i-C₃H₇ 173 ″ ″ ″ n-C₄H₉ 174 ″ ″ ″ i-C₄H₉ 175 ″ ″ ″ s-C₄H₉ 176 ″ ″ ″ t-C₄H₉ 177 ″ ″ ″ n-C₆H₁₃ 178 ″ ″ ″ CH₂-t-Bu 179 ″ ″ ″ CF₃ 180 ″ ″ ″ C₂F₅ 181 ″ ″ ″ n-C₃F₇ 182 ″ ″ ″ n-C₄F₉ NMR 183 ″ ″ ″ n-C₅F₁₁ 184 ″ ″ ″ n-C₆F₁₃ NMR 185 ″ ″ ″ phenyl 186 ″ ″ ″ 2-F-phenyl 187 ″ ″ ″ 3-F-phenyl 188 ″ ″ ″ 4-F-phenyl 189 ″ ″ ″ 2-Cl-phenyl 190 ″ ″ ″ 3-Cl-phenyl 191 ″ ″ ″ 4-Cl-phenyl NMR 192 ″ ″ ″ 2,4-Cl₂-phenyl 193 ″ ″ ″ 3,4-Cl₂-phenyl 194 ″ ″ ″ 2,5-Cl₂-phenyl 195 ″ ″ ″ 2,6-Cl₂-phenyl 196 ″ ″ ″ 2-CF₃-phenyl 197 ″ ″ ″ 3-CF₃-phenyl 198 ″ ″ ″ 3,5-(CF₃)₂-phenyl 199 ″ ″ ″ 4-CF₃-phenyl 200 ″ ″ ″ 2-CH₃-phenyl 201 ″ ″ ″ 4-CH₃-phenyl 202 ″ ″ ″ 2,4-(CH₃)₂-phenyl 203 ″ ″ ″ 2,6-(CH₃)₂-phenyl 204 ″ ″ ″ 2,4,6-(CH₃)₃-phenyl 205 ″ ″ ″ 2-CH₃O-phenyl NMR 206 ″ ″ ″ 4-CH₃O-phenyl 207 ″ ″ ″ 4-C₂H₅O-phenyl 208 ″ ″ ″ 4-CF₃O-phenyl 209 ″ ″ ″ 4-CN-phenyl 210 ″ ″ ″ 3-NO₂-phenyl 211 ″ ″ ″ 4-NO₂-phenyl 212 Cl H H CH₃ 213 ″ ″ ″ C₂H₅ 214 ″ ″ ″ n-C₃H₇ 215 ″ ″ ″ i-C₃H₇ 216 ″ ″ ″ n-C₄H₉ 217 ″ ″ ″ n-C₄H₉ 218 ″ ″ ″ s-C₄H₉ 219 ″ ″ ″ t-C₄H₉ 220 ″ ″ ″ n-C₆H₁₃ 221 ″ ″ ″ CH₂-t-Bu 222 ″ ″ ″ CF₃ 223 ″ ″ ″ C₂F₅ 224 ″ ″ ″ n-C₃F₇ 225 ″ ″ ″ n-C₄H₉ NMR 226 ″ ″ ″ n-C₅H₁₁ 227 ″ ″ ″ n-C₆H₁₃ NMR 228 ″ ″ ″ phenyl 229 ″ ″ ″ 2-F-phenyl 230 ″ ″ ″ 3-F-phenyl 231 ″ ″ ″ 4-F-phenyl 232 ″ ″ ″ 2-Cl-phenyl 233 ″ ″ ″ 3-Cl-phenyl 234 ″ ″ ″ 4-Cl-phenyl NMR 235 ″ ″ ″ 2,4-Cl₂-phenyl 236 ″ ″ ″ 3,4-Cl₂-phenyl 237 ″ ″ ″ 2,5-Cl₂-phenyl 238 ″ ″ ″ 2,6-Cl₂-phenyl 239 ″ ″ ″ 2-CF₃-phenyl 240 ″ ″ ″ 3-CF₃-phenyl 241 ″ ″ ″ 3,5-(CF₃)₂-phenyl 242 ″ ″ ″ 4-CF₃-phenyl 243 ″ ″ ″ 2-CH₃-phenyl 244 ″ ″ ″ 4-CH₃-phenyl 245 ″ ″ ″ 2,4-(CH₃)₂-phenyl 246 ″ ″ ″ 2,6-(CH₃)₂-phenyl 247 ″ ″ ″ 2,4,6-(CH₃)₃-phenyl 248 ″ ″ ″ 2-CH₃O-phenyl 249 ″ ″ ″ 4-CH₃O-phenyl 250 ″ ″ ″ 4-C₂H₅O-phenyl 251 ″ ″ ″ 4-CF₃O-phenyl 252 ″ ″ ″ 4-CN-phenyl 253 ″ ″ ″ 3-NO₂-phenyl 254 ″ ″ ″ 4-NO₂-phenyl 255 CH₃ H H CH₃ 256 ″ ″ ″ C₂H₅ 257 ″ ″ ″ n-C₃H₇ 258 ″ ″ ″ i-C₃H₇ 259 ″ ″ ″ n-C₄H₉ 260 ″ ″ ″ i-C₄H₉ 261 ″ ″ ″ s-C₄H₉ 262 ″ ″ ″ t-C₄H₉ 263 ″ ″ ″ n-C₆H₁₃ 264 ″ ″ ″ CH₂-t-Bu 265 ″ ″ ″ CF₃ 266 ″ ″ ″ C₂F₅ 267 ″ ″ ″ n-C₃F₇ 268 ″ ″ ″ n-C₄H₉ 269 ″ ″ ″ n-C₅F₁₁ 270 ″ ″ ″ n-C₆F₁₃ 271 ″ ″ ″ phenyl 272 ″ ″ ″ 2-F-phenyl 273 ″ ″ ″ 3-F-phenyl 274 ″ ″ ″ 4-F-phenyl 275 ″ ″ ″ 2-Cl-phenyl 276 ″ ″ ″ 3-Cl-phenyl 277 ″ ″ ″ 4-Cl-phenyl 278 ″ ″ ″ 2,4-Cl₂-phenyl 279 ″ ″ ″ 3,4-Cl₂-phenyl 280 ″ ″ ″ 2,5-Cl₂-phenyl 281 ″ ″ ″ 2,6-Cl₂-phenyl 282 ″ ″ ″ 2-CF₃-phenyl 283 ″ ″ ″ 3-CF₃-phenyl 284 ″ ″ ″ 3,5-(CF₃)₂-phenyl 285 ″ ″ ″ 4-CF₃-phenyl 286 ″ ″ ″ 2-CH₃-phenyl 287 ″ ″ ″ 4-CH₃-phenyl 288 ″ ″ ″ 2,4-(CH₃)₂-phenyl 289 ″ ″ ″ 2,6-(CH₃)₂-phenyl 290 ″ ″ ″ 2,4,6-(CH₃)₃-phenyl 291 ″ ″ ″ 2-CH₃O-phenyl 292 ″ ″ ″ 4-CH₃O-phenyl 293 ″ ″ ″ 4-C₂H₅O-phenyl 294 ″ ″ ″ 4-CF₃O-phenyl 295 ″ ″ ″ 4-CN-phenyl 296 ″ ″ ″ 3-NO₂-phenyl 297 ″ ″ ″ 4-NO₂-phenyl 298 Br H H CH₃ 299 ″ ″ ″ C₂H₅ 300 ″ ″ ″ n-C₃H₇ 301 ″ ″ ″ i-C₃H₇ 302 ″ ″ ″ n-C₄H₉ 303 ″ ″ ″ i-C₄H₉ 304 ″ ″ ″ s-C₄H₉ 305 ″ ″ ″ t-C₄H₉ NMR 306 ″ ″ ″ n-C₆H₁₃ 307 ″ ″ ″ CH₂-t-Bu 308 ″ ″ ″ CF₃ 309 ″ ″ ″ C₂F₅ 310 ″ ″ ″ n-C₃F₇ 311 ″ ″ ″ n-C₄F₉ NMR 312 ″ ″ ″ n-C₅F₁₁ 313 ″ ″ ″ n-C₆F₁₃ 314 ″ ″ ″ phenyl 315 ″ ″ ″ 2-F-phenyl 316 ″ ″ ″ 3-F-phenyl 317 ″ ″ ″ 4-F-phenyl 318 ″ ″ ″ 2-Cl-phenyl 319 ″ ″ ″ 3-Cl-phenyl 320 ″ ″ ″ 4-Cl-phenyl 321 ″ ″ ″ 2,4-Cl₂-phenyl 322 ″ ″ ″ 3,4-Cl₂-phenyl 323 ″ ″ ″ 2,5-Cl₂-phenyl 324 ″ ″ ″ 2,6-Cl₂-phenyl 325 ″ ″ ″ 2-CF₃-phenyl 326 ″ ″ ″ 3-CF₃-phenyl 327 ″ ″ ″ 3,5-(CF₃)₂-phenyl 328 ″ ″ ″ 4-CF₃-phenyl NMR 329 ″ ″ ″ 2-CH₃-phenyl 330 ″ ″ ″ 4-CH₃-phenyl 331 ″ ″ ″ 2,4-(CH₃)₂-phenyl 332 ″ ″ ″ 2,6-(CH₃)₂-phenyl 333 ″ ″ ″ 2,4,6-(CH₃)₃-phenyl 334 ″ ″ ″ 2-CH₃O-phenyl NMR 335 ″ ″ ″ 4-CH₃O-phenyl 336 ″ ″ ″ 4-C₂H₅O-phenyl 337 ″ ″ ″ 4-CF₃O-phenyl 338 ″ ″ ″ 4-CN-phenyl 339 ″ ″ ″ 3-NO₂-phenyl 340 ″ ″ ″ 4-NO₂-phenyl 341 CH₃ CH₃ H CH₃ 342 ″ ″ ″ C₂H₅ 343 ″ ″ ″ n-C₃H₇ 344 ″ ″ ″ i-C₃H₇ 345 ″ ″ ″ n-C₄H₉ 346 ″ ″ ″ i-C₄H₉ 347 ″ ″ ″ s-C₄H₉ 348 ″ ″ ″ t-C₄H₉ 349 ″ ″ ″ n-C₆H₉ 350 ″ ″ ″ CH₂-t-Bu 351 ″ ″ ″ CF₃ 352 ″ ″ ″ C₂F₅ 353 ″ ″ ″ n-C₃F₇ 354 ″ ″ ″ n-C₄F₉ NMR 355 ″ ″ ″ n-C₅F₁₁ 356 ″ ″ ″ n-C₆F₁₃ NMR 357 ″ ″ ″ phenyl 358 ″ ″ ″ 2-F-phenyl 359 ″ ″ ″ 3-F-phenyl 360 ″ ″ ″ 4-F-phenyl 361 ″ ″ ″ 2-Cl-phenyl 362 ″ ″ ″ 3-Cl-phenyl 363 ″ ″ ″ 4-Cl-phenyl NMR 364 ″ ″ ″ 2,4-Cl₂-phenyl 365 ″ ″ ″ 3,4-Cl₂-phenyl 366 ″ ″ ″ 2,5-Cl₂-phenyl 367 ″ ″ ″ 2,6-Cl₂-phenyl 368 ″ ″ ″ 2-CF₃-phenyl 369 ″ ″ ″ 3-CF₃-phenyl 370 ″ ″ ″ 3,5-(CF₃)₂-phenyl 371 ″ ″ ″ 4-CF₃-phenyl 372 ″ ″ ″ 2-CH₃-phenyl 373 ″ ″ ″ 4-CH₃-phenyl 374 ″ ″ ″ 2,4-(CH₃)₂-phenyl 375 ″ ″ ″ 2,6-(CH₃)₂-phenyl 376 ″ ″ ″ 2,4,6-(CH₃)₃-phenyl 378 ″ ″ ″ 2-CH₃O-phenyl 379 ″ ″ ″ 4-CH₃O-phenyl 380 ″ ″ ″ 4-C₂H₅O-phenyl 381 ″ ″ ″ 4-CF₃O-phenyl 382 ″ ″ ″ 4-CN-phenyl 383 ″ ″ ″ 3-NO₂-phenyl 384 ″ ″ ″ 4-NO₂-phenyl

[0242] TABLE 2 Oxazolines, pyrrolines and imidazolines of the formula (I), G = 3-isoxazolinyl

Ex. Physical No. X¹ X² Z R⁵ data 385 F F CH₂ CH₃ 386 ″ ″ ″ C₂H₅ 387 ″ ″ ″ n-C₃H₇ 388 ″ ″ ″ i-C₃H₇ 389 ″ ″ ″ n-C₄H₉ 390 ″ ″ ″ i-C₄H₉ 400 ″ ″ ″ s-C₄H₉ 401 ″ ″ ″ t-C₄H₉ 402 ″ ″ ″ n-C₆H₁₃ 403 ″ ″ ″ CH₂-t-Bu 404 ″ ″ ″ CF₃ 405 ″ ″ ″ C₂F₅ 406 ″ ″ ″ n-C₃F₇ 407 ″ ″ ″ n-C₄F₉ 408 ″ ″ ″ n-C₅F₁₁ 409 ″ ″ ″ n-C₆F₁₃ 410 ″ ″ ″ phenyl 411 ″ ″ ″ 2-F-phenyl 412 ″ ″ ″ 3-F-phenyl 413 ″ ″ ″ 4-F-phenyl 414 ″ ″ ″ 2-Cl-phenyl 415 ″ ″ ″ 3-Cl-phenyl 416 ″ ″ ″ 4-Cl-phenyl 417 ″ ″ ″ 2,4-Cl₂-phenyl 418 ″ ″ ″ 3,4-Cl₂-phenyl 419 ″ ″ ″ 2,5-Cl₂-phenyl 420 ″ ″ ″ 2,6-Cl₂-phenyl 421 ″ ″ ″ 2-CF₃-phenyl 422 ″ ″ ″ 3-CF₃-phenyl 423 ″ ″ ″ 3,5-(CF₃)₂-phenyl 424 ″ ″ ″ 4-CF₃-phenyl 425 ″ ″ ″ 2-CH₃-phenyl 426 ″ ″ ″ 4-CH₃-phenyl 427 ″ ″ ″ 2,4-(CH₃)₂-phenyl 428 ″ ″ ″ 2,6-(CH₃)₂-phenyl 429 ″ ″ ″ 2,4,6-(CH₃)₃-phenyl 430 ″ ″ ″ 2-CH₃O-phenyl 431 ″ ″ ″ 4-CH₃O-phenyl 432 ″ ″ ″ 4-C₂H₅O-phenyl 433 ″ ″ ″ 4-CF₃O-phenyl 434 ″ ″ ″ 4-CN-phenyl 435 ″ ″ ″ 3-NO₂-phenyl 436 ″ ″ ″ 4-NO₂-phenyl 437 F H CH₂ CH₃ 438 ″ ″ ″ C₂H₅ 439 ″ ″ ″ n-C₃H₇ 440 ″ ″ ″ i-C₃H₇ 441 ″ ″ ″ n-C₄H₉ 442 ″ ″ ″ i-C₄H₉ 443 ″ ″ ″ s-C₄H₉ 444 ″ ″ ″ t-C₄H₉ 445 ″ ″ ″ n-C₆H₁₃ 446 ″ ″ ″ CH₂-t-Bu 447 ″ ″ ″ CF₃ 448 ″ ″ ″ C₂F₅ 449 ″ ″ ″ n-C₃F₇ 450 ″ ″ ″ n-C₄F₉ 451 ″ ″ ″ n-C₅F₁₁ 452 ″ ″ ″ n-C₆F₁₃ 453 ″ ″ ″ phenyl 454 ″ ″ ″ 2-F-phenyl 455 ″ ″ ″ 3-F-phenyl 456 ″ ″ ″ 4-F-phenyl 457 ″ ″ ″ 2-Cl-phenyl 458 ″ ″ ″ 3-Cl-phenyl 459 ″ ″ ″ 4-Cl-phenyl 460 ″ ″ ″ 2,4-Cl₂-phenyl 461 ″ ″ ″ 3,4-Cl₂-phenyl 462 ″ ″ ″ 2,5-Cl₂-phenyl 463 ″ ″ ″ 2,6-Cl₂-phenyl 464 ″ ″ ″ 2-CF₃-phenyl 465 ″ ″ ″ 3-CF₃-phenyl 466 ″ ″ ″ 3,5-(CF₃)₂-phenyl 467 ″ ″ ″ 4-CF₃-phenyl 468 ″ ″ ″ 2-CH₃-phenyl 469 ″ ″ ″ 4-CH₃-phenyl 470 ″ ″ ″ 2,4-(CH₃)₂-phenyl 471 ″ ″ ″ 2,6-(CH₃)₂-phenyl 472 ″ ″ ″ 2,4,6-(CH₃)₃-phenyl 473 ″ ″ ″ 2-CH₃O-phenyl 474 ″ ″ ″ 4-CH₃O-phenyl 475 ″ ″ ″ 4-C₂H₅O-phenyl 476 ″ ″ ″ 4-CF₃O-phenyl 477 ″ ″ ″ 4-CN-phenyl 478 ″ ″ ″ 3-NO₂-phenyl 479 ″ ″ ″ 3-NO₂-phenyl 480 F Cl CH₂ CH₃ 481 ″ ″ ″ C₂H₅ 482 ″ ″ ″ n-C₃H₇ 483 ″ ″ ″ i-C₃H₇ 484 ″ ″ ″ n-C₄H₉ 485 ″ ″ ″ i-C₄H₉ 486 ″ ″ ″ s-C₄H₉ 487 ″ ″ ″ t-C₄H₉ 488 ″ ″ ″ n-C₆H₁₃ 489 ″ ″ ″ CH₂-t-Bu 490 ″ ″ ″ CF₃ 491 ″ ″ ″ C₂F₅ 492 ″ ″ ″ n-C₃F₇ 493 ″ ″ ″ n-C₄F₉ 494 ″ ″ ″ n-C₅F₁₁ 495 ″ ″ ″ n-C₆F₁₃ 496 ″ ″ ″ phenyl 497 ″ ″ ″ 2-F-phenyl 498 ″ ″ ″ 3-F-phenyl 499 ″ ″ ″ 4-F-phenyl 500 ″ ″ ″ 2-Cl-phenyl 501 ″ ″ ″ 3-Cl-phenyl 502 ″ ″ ″ 4-Cl-phenyl 503 ″ ″ ″ 2,4-Cl₂-phenyl 504 ″ ″ ″ 3,4-Cl₂-phenyl 505 ″ ″ ″ 2,5-Cl₂-phenyl 506 ″ ″ ″ 2,6-Cl₂-phenyl 507 ″ ″ ″ 2-CF₃-phenyl 508 ″ ″ ″ 3-CF₃-phenyl 509 ″ ″ ″ 3,5-(CF₃)₂-phenyl 510 ″ ″ ″ 4-CF₃-phenyl 511 ″ ″ ″ 2-CH₃-phenyl 512 ″ ″ ″ 4-CF₃-phenyl 513 ″ ″ ″ 2,4-(CH₃)₂-phenyl 514 ″ ″ ″ 2,6-(CH₃)₂-phenyl 515 ″ ″ ″ 2,4,6-(CH₃)₃-phenyl 516 ″ ″ ″ 2-CH₃O-phenyl 517 ″ ″ ″ 4-CH₃O-phenyl 518 ″ ″ ″ 4-C₂H₅O-phenyl 519 ″ ″ ″ 4-CF₃O-phenyl 520 ″ ″ ″ 4-CN-phenyl 521 ″ ″ ″ 3-NO₂-phenyl 522 ″ ″ ″ 3-NO₂-phenyl 523 F F NCOOEt CH₃ 524 ″ ″ ″ C₂H₅ 525 ″ ″ ″ n-C₃H₇ 526 ″ ″ ″ i-C₃H₇ 527 ″ ″ ″ n-C₄H₉ 528 ″ ″ ″ i-C₄H₉ 529 ″ ″ ″ s-C₄H₉ 530 ″ ″ ″ t-C₄H₉ 531 ″ ″ ″ n-C₆H₁₃ 532 ″ ″ ″ CH₂-t-Bu 533 ″ ″ ″ CF₃ 534 ″ ″ ″ C₂F₅ 535 ″ ″ ″ n-C₃F₇ 536 ″ ″ ″ n-C₄F₉ 537 ″ ″ ″ n-C₅F₁₁ 538 ″ ″ ″ n-C₆F₁₃ 539 ″ ″ ″ phenyl 540 ″ ″ ″ 2-F-phenyl 541 ″ ″ ″ 3-F-phenyl 542 ″ ″ ″ 4-F-phenyl 543 ″ ″ ″ 2-Cl-phenyl 544 ″ ″ ″ 3-Cl-phenyl 545 ″ ″ ″ 4-Cl-phenyl 546 ″ ″ ″ 2,4-Cl₂-phenyl 547 ″ ″ ″ 3,4-Cl₂-phenyl 548 ″ ″ ″ 2,5-Cl₂-phenyl 549 ″ ″ ″ 2,6-Cl₂-phenyl 550 ″ ″ ″ 2-CF₃-phenyl 551 ″ ″ ″ 3-CF₃-phenyl 552 ″ ″ ″ 3,5-(CF₃)₂-phenyl 553 ″ ″ ″ 4-CF₃-phenyl 554 ″ ″ ″ 2-CH₃-phenyl 555 ″ ″ ″ 4-CH₃-phenyl 556 ″ ″ ″ 2,4-(CH₃)₂-phenyl 557 ″ ″ ″ 2,6-(CH₃)₂-phenyl 558 ″ ″ ″ 2,4,6-(CH₃)₃-phenyl 559 ″ ″ ″ 2-CH₃O-phenyl 560 ″ ″ ″ 4-CH₃O-phenyl 561 ″ ″ ″ 4-C₂H₅O-phenyl 562 ″ ″ ″ 4-CF₃O-phenyl 563 ″ ″ ″ 4-CN-phenyl 564 ″ ″ ″ 3-NO₂-phenyl 565 ″ ″ ″ 4-NO₂-phenyl

[0243] TABLE 3 Oxazolines of the formula (I), Z = O, G = 5-isoxazolinyl

Ex. Physical No. X¹ X² R⁵ data 566 F F CH₃ NMR 567 ″ ″ C₂H₅ NMR 568 ″ ″ n-C₃H₇ NMR 569 ″ ″ i-C₃H₇ NMR 570 ″ ″ n-C₄H₉ NMR 571 ″ ″ i-C₄H₉ 572 ″ ″ s-C₄H₉ 573 ″ ″ t-C₄H₉ NMR 574 ″ ″ n-C₅H₁₁ NMR 575 ″ ″ n-C₆H₁₃ 576 ″ ″ CH(C₂H₅)₂ NMR 577 ″ ″ CH₂-t-Bu 578 ″ ″ CH₂CF₃ NMR 579 ″ ″ C₂H₄CF₃ NMR 580 ″ ″ CF₃ 581 ″ ″ C₂F₅ 582 ″ ″ n-C₃F₇ 583 ″ ″ n-C₄F₉ 584 ″ ″ n-C₅F₁₁ 585 ″ ″ n-C₆F₁₃ 586 ″ ″ phenyl 587 ″ ″ 2-F-phenyl 588 ″ ″ 3-F-phenyl 589 ″ ″ 4-F-phenyl NMR 590 ″ ″ 2-Cl-phenyl 591 ″ ″ 3-Cl-phenyl 592 ″ ″ 4-Cl-phenyl NMR 593 ″ ″ 2,4-Cl₂-phenyl 594 ″ ″ 3,4-Cl₂-phenyl 595 ″ ″ 2,5-Cl₂-phenyl 596 ″ ″ 2,6-Cl₂-phenyl 597 ″ ″ 2-CF₃-phenyl 598 ″ ″ 3-CF₃-phenyl 599 ″ ″ 3,5-(CF₃)₂-phenyl 600 ″ ″ 4-CF₃-phenyl NMR 601 ″ ″ 2-CH₃-phenyl 602 ″ ″ 4-CH₃-phenyl 603 ″ ″ 2,4-(CH₃)₂-phenyl 604 ″ ″ 2,6-(CH₃)₂-phenyl 605 ″ ″ 2,4,6-(CH₃)₃-phenyl NMR 606 ″ ″ 2-CH₃O-phenyl 607 ″ ″ 4-CH₃O-phenyl 608 ″ ″ 4-C₂H₅O-phenyl 609 ″ ″ 4-CF₃O-phenyl 610 ″ ″ 4-CN-phenyl 611 ″ ″ 3-NO₂-phenyl 612 ″ ″ 4-NO₂-phenyl 613 ″ ″ COOH NMR 614 ″ ″ COOC₂H₅ NMR 615 ″ ″ COOCH₂CF₃ NMR 616 ″ ″ COOC₂H₄CF₃ NMR 617 ″ ″ CONH₂ 618 ″ ″ CONHCH₃ 619 ″ ″ CONHC₂H₅ NMR 620 ″ ″ CON(CH₃)₂ 621 ″ ″ CON(C₂H₅)₂ NMR 622 ″ ″ CONH(n-C₃H₇) NMR 623 ″ ″ CONHCH₂C₂F₅ NMR 624 ″ ″ CONHCH₂C₂H₃ NMR 625 ″ ″ CONHCH₂C₂H₃ NMR 626 ″ ″ CONHCH₂C₃F₇ NMR 627 ″ ″ CONH-s-C₅H₁₁ NMR 628 ″ ″ CONHCH₂CF₃ NMR 629 ″ ″ CONHC₃H₆OCH₃ NMR 630 ″ ″ CONHCH₂-(2-tetrahydrofuranyl) NMR 631 ″ ″ CONHCH₂-(2,6-F₂-phenyl) NMR 632 ″ ″ CONHCH₂-(4-F-phenyl) 633 ″ ″ CONHCH₂-(3-CF₃-phenyl) NMR 634 ″ ″ CONHCH₂-(4-CF₃-phenyl) 635 ″ ″ CONH(2,5-F₂-phenyl) 636 ″ ″ CONH(4-F-phenyl) 637 ″ ″ CONH(3-CF₃-phenyl) 638 ″ ″ CONH(4-CF₃-phenyl) 639 F H CH₃ 640 ″ ″ C₂H₅ 641 ″ ″ n-C₃H₇ 642 ″ ″ i-C₃H₇ 643 ″ ″ n-C₄H₉ 644 ″ ″ i-C₄H₉ 645 ″ ″ s-C₄H₉ 646 ″ ″ t-C₄H₉ 647 ″ ″ n-C₅H₁₁ 648 ″ ″ n-C₆H₁₃ 649 ″ ″ CH(C₂H₅)₂ 650 ″ ″ CH₂-t-Bu 651 ″ ″ CH₂CF₃ 652 ″ ″ C₂H₄CF₃ 653 ″ ″ CF₃ 654 ″ ″ C₂H₅ 655 ″ ″ n-C₃H₇ 656 ″ ″ n-C₄F₉ 657 ″ ″ n-C₅F₁₁ 658 ″ ″ n-C₆F₁₃ 659 ″ ″ phenyl 660 ″ ″ 2-F-phenyl 661 ″ ″ 3-F-phenyl 662 ″ ″ 4-F-phenyl 663 ″ ″ 2-Cl-phenyl 664 ″ ″ 3-Cl-phenyl 665 ″ ″ 4-Cl-phenyl 666 ″ ″ 2,4-Cl₂-phenyl 667 ″ ″ 3,4-Cl₂-phenyl 668 ″ ″ 2,5-Cl₂-phenyl 669 ″ ″ 2,6-Cl₂-phenyl 670 ″ ″ 2-CF₃-phenyl 671 ″ ″ 3-CF₃-phenyl 672 ″ ″ 3,5-(CF₃)₂-phenyl 673 ″ ″ 4-CF₃-phenyl 674 ″ ″ 2-CH₃-phenyl 675 ″ ″ 4-CH₃-phenyl 676 ″ ″ 2,4-(CH₃)₂-phenyl 677 ″ ″ 2,6-(CH₃)₂-phenyl 678 ″ ″ 2,4,6-(CH₃)₃-phenyl 679 ″ ″ 2-CH₃O-phenyl 680 ″ ″ 4-CH₃O-phenyl 681 ″ ″ 4-C₂H₅O-phenyl 682 ″ ″ 4-CF₃O-phenyl 683 ″ ″ 4-CN-phenyl 684 ″ ″ 3-NO₂-phenyl 685 ″ ″ 4-NO₂-phenyl 686 F H CH₃ 687 ″ ″ C₂H₅ 688 ″ ″ n-C₃H₇ 689 ″ ″ i-C₃H₇ 690 ″ ″ n-C₄H₉ 691 ″ ″ i-C₄H₉ 692 ″ ″ s-C₄H₉ 693 ″ ″ t-C₄H₉ 694 ″ ″ n-C₅H₁₁ 695 ″ ″ n-C₆H₁₃ 696 ″ ″ CH(C₂H₅)₂ 697 ″ ″ CH₂-t-Bu 698 ″ ″ CH₂CF₃ 699 ″ ″ C₂H₄CF₃ 700 ″ ″ CF₃ 701 ″ ″ C₂F₅ 702 ″ ″ n-C₃F₇ 703 ″ ″ n-C₄F₉ 704 ″ ″ n-C₅F₁₁ 705 ″ ″ n-C₆F₁₃ 706 ″ ″ phenyl 707 ″ ″ 2-F-phenyl 708 ″ ″ 3-F-phenyl 709 ″ ″ 4-F-phenyl 710 ″ ″ 2-Cl-phenyl 711 ″ ″ 3-Cl-phenyl 712 ″ ″ 4-Cl-phenyl 713 ″ ″ 2,4-Cl₂-phenyl 714 ″ ″ 3,4-Cl₂-phenyl 715 ″ ″ 2,5-Cl₂-phenyl 716 ″ ″ 2,6-Cl₂-phenyl 717 ″ ″ 2-CF₃-phenyl 718 ″ ″ 3-CF₃-phenyl 719 ″ ″ 3,5-(CF₃)₂-phenyl 720 ″ ″ 4-CF₃-phenyl 721 ″ ″ 2-CH₃-phenyl 722 ″ ″ 4-CH₃-phenyl 723 ″ ″ 2,4-(CH₃)₂-phenyl 724 ″ ″ 2,6-(CH₃)₂-phenyl 725 ″ ″ 2,4,6-(CH₃)₃-phenyl 726 ″ ″ 2-CH₃O-phenyl 727 ″ ″ 4-CH₃O-phenyl 728 ″ ″ 4-C₂H₅O-phenyl 729 ″ ″ 4-CF₃O-phenyl 730 ″ ″ 4-CN-phenyl 731 ″ ″ 3-NO₂-phenyl 732 ″ ″ 4-NO₂-phenyl 733 Cl H CH₃ 734 ″ ″ C₂H₅ 735 ″ ″ n-C₃H₇ 736 ″ ″ i-C₃H₇ 737 ″ ″ n-C₄H₉ 738 ″ ″ i-C₄H₉ 739 ″ ″ s-C₄H₉ 740 ″ ″ t-C₄H₉ 741 ″ ″ n-C₅H₁₃ 742 ″ ″ n-C₆H₁₃ 743 ″ ″ CH(C₂H₅)₂ 744 ″ ″ CH₂-t-Bu 745 ″ ″ CH₂CF₃ 746 ″ ″ C₂H₄CF₃ 747 ″ ″ CF₃ 748 ″ ″ C₂F₅ 749 ″ ″ n-C₃F₇ 750 ″ ″ n-C₄F₉ 751 ″ ″ n-C₅F₁₁ 752 ″ ″ n-C₆F₁₃ 753 ″ ″ phenyl 754 ″ ″ 2-F-phenyl 755 ″ ″ 3-F-phenyl 756 ″ ″ 4-F-phenyl 757 ″ ″ 2-Cl-phenyl 758 ″ ″ 3-Cl-phenyl 759 ″ ″ 4-Cl-phenyl 760 ″ ″ 2,4-Cl₂-phenyl 761 ″ ″ 3,4-Cl₂-phenyl 762 ″ ″ 2,5-Cl₂-phenyl 763 ″ ″ 2,6-Cl₂-phenyl 764 ″ ″ 2-CF₃-phenyl 765 ″ ″ 3-CF₃-phenyl 767 ″ ″ 3,5-(CF₃)₂-phenyl 768 ″ ″ 4-CF₃-phenyl 769 ″ ″ 2-CH₃-phenyl 770 ″ ″ 4-CH₃-phenyl 771 ″ ″ 2,4-(CH₃)₂-phenyl 772 ″ ″ 2,6-(CH₃)₂-phenyl 773 ″ ″ 2,4,6-(CH₃)₃-phenyl 774 ″ ″ 2-CH₃O-phenyl 776 ″ ″ 4-CH₃O-phenyl 777 ″ ″ 4-C₂H₅O-phenyl 778 ″ ″ 4-CF₃O-phenyl 779 ″ ″ 4-CN-phenyl 780 ″ ″ 3-NO₂-phenyl 781 ″ ″ 2-NO₂-phenyl 782 CH₃ H CH₃ 783 ″ ″ C₂H₅ 784 ″ ″ n-C₃H₇ 785 ″ ″ i-C₃H₇ 786 ″ ″ n-C₄H₉ 787 ″ ″ i-C₄H₉ 788 ″ ″ s-C₄H₉ 789 ″ ″ t-C₄H₉ 790 ″ ″ n-C₅H₁₁ 791 ″ ″ n-C₆H₁₃ 792 ″ ″ CH(C₂H₅)₂ 793 ″ ″ CH₂-t-Bu 794 ″ ″ CH₂CF₃ 795 ″ ″ C₂H₄CF₃ 796 ″ ″ CF₃ 797 ″ ″ C₂F₅ 798 ″ ″ n-C₃F₇ 799 ″ ″ n-C₄F₉ 800 ″ ″ n-C₅F₁₁ 801 ″ ″ n-C₆F₁₃ 802 ″ ″ phenyl 803 ″ ″ 2-F-phenyl 804 ″ ″ 3-F-phenyl 805 ″ ″ 4-F-phenyl 806 ″ ″ 2-Cl-phenyl 807 ″ ″ 3-Cl-phenyl 808 ″ ″ 4-Cl-phenyl 809 ″ ″ 2,4-Cl₂-phenyl 810 ″ ″ 3,4-Cl₂-phenyl 811 ″ ″ 2,5-Cl₂-phenyl 812 ″ ″ 2,6-Cl₂-phenyl 813 ″ ″ 2-CF₃-phenyl 814 ″ ″ 3-CF₃-phenyl 815 ″ ″ 3,5-(CF₃)₂-phenyl 816 ″ ″ 4-CF₃-phenyl 817 ″ ″ 2-CH₃-phenyl 818 ″ ″ 4-CH₃-phenyl 819 ″ ″ 2,4-(CH₃)₂-phenyl 820 ″ ″ 2,6-(CH₃)₂-phenyl 821 ″ ″ 2,4,6-(CH₃)₃-phenyl 822 ″ ″ 2-CH₃O-phenyl 823 ″ ″ 4-CH₃O-phenyl 824 ″ ″ 4-C₂H₅O-phenyl 825 ″ ″ 4-CF₃O-phenyl 826 ″ ″ 4-CN-phenyl 827 ″ ″ 3-NO₂-phenyl 828 ″ ″ 2-NO₂-phenyl 829 Br H CH₃ 830 ″ ″ C₂H₅ 831 ″ ″ n-C₃H₇ 832 ″ ″ i-C₃H₇ 833 ″ ″ n-C₄H₉ 834 ″ ″ i-C₄H₉ 835 ″ ″ s-C₄H₉ 836 ″ ″ t-C₄H₉ 837 ″ ″ n-C₅H₁₁ 838 ″ ″ n-C₆H₁₃ 839 ″ ″ CH(C₂H₅)₂ 840 ″ ″ CH₂-t-Bu 841 ″ ″ CH₂CF₃ 842 ″ ″ C₂H₄CF₃ 843 ″ ″ CF₃ 844 ″ ″ C₂F₅ 845 ″ ″ n-C₃F₇ 846 ″ ″ n-C₄F₉ 847 ″ ″ n-C₅F₁₁ 848 ″ ″ n-C₆F₁₃ 849 ″ ″ phenyl 850 ″ ″ 2-F-phenyl 851 ″ ″ 3-F-phenyl 852 ″ ″ 4-F-phenyl 853 ″ ″ 2-Cl-phenyl 854 ″ ″ 3-Cl-phenyl 855 ″ ″ 4-Cl-phenyl 856 ″ ″ 2,4-Cl₂-phenyl 857 ″ ″ 3,4-Cl₂-phenyl 858 ″ ″ 2,5-Cl₂-phenyl 859 ″ ″ 2,6-Cl₂-phenyl 860 ″ ″ 2-CF₃-phenyl 861 ″ ″ 3-CF₃-phenyl 862 ″ ″ 3,5-(CF₃)₂-phenyl 863 ″ ″ 4-CF₃-phenyl 864 ″ ″ 2-CH₃-phenyl 865 ″ ″ 4-CH₃-phenyl 866 ″ ″ 2,4-(CH₃)₂-phenyl 867 ″ ″ 2,6-(CH₃)₂-phenyl 868 ″ ″ 2,4,6-(CH₃)₃-phenyl 869 ″ ″ 2-CH₃O-phenyl 870 ″ ″ 4-CH₃O-phenyl 871 ″ ″ 4-C₂H₅O-phenyl 872 ″ ″ 4-CF₃O-phenyl 873 ″ ″ 4-CN-phenyl 874 ″ ″ 3-NO₂-phenyl 875 ″ ″ 2-NO₂-phenyl

[0244] TABLE 4 Pyrrolines and imidazolines of the formula (I), G = 5-isoxazolinyl

Ex. No. X¹ X² Z R⁵ Physical data 876 F F CH₂ CH₃ 877 ″ ″ ″ C₂H₅ 878 ″ ″ ″ n-C₃H₇ 879 ″ ″ ″ i-C₃H₇ 880 ″ ″ ″ n-C₄H₉ 881 ″ ″ ″ i-C₄H₉ 882 ″ ″ ″ s-C₄H₉ 883 ″ ″ ″ t-C₄H₉ 884 ″ ″ ″ n-C₆H₁₃ 885 ″ ″ ″ CH₂-t-Bu 886 ″ ″ ″ CF₃ 887 ″ ″ ″ C₂F₅ 888 ″ ″ ″ n-C₃F₇ 889 ″ ″ ″ n-C₄F₉ 890 ″ ″ ″ n-C₅F₁₁ 891 ″ ″ ″ n-C₆F₁₃ 892 ″ ″ ″ phenyl 893 ″ ″ ″ 2-F-phenyl 894 ″ ″ ″ 3-F-phenyl 895 ″ ″ ″ 4-F-phenyl 896 ″ ″ ″ 2-Cl-phenyl 897 ″ ″ ″ 3-Cl-phenyl 898 ″ ″ ″ 4-Cl-phenyl 899 ″ ″ ″ 2,4-Cl₂-phenyl 900 ″ ″ ″ 3,4-Cl₂-phenyl 901 ″ ″ ″ 2,5-Cl₂-phenyl 902 ″ ″ ″ 2,6-Cl₂-phenyl 903 ″ ″ ″ 2-CF₃-phenyl 904 ″ ″ ″ 3-CF₃-phenyl 905 ″ ″ ″ 3,5-(CF₃)₂-phenyl 906 ″ ″ ″ 4-CF₃-phenyl 907 ″ ″ ″ 2-CH₃-phenyl 908 ″ ″ ″ 4-CH₃-phenyl 909 ″ ″ ″ 2,4-(CH₃)₂-phenyl 910 ″ ″ ″ 2,6-(CH₃)₂-phenyl 911 ″ ″ ″ 2,4,6-(CH₃)₃-phenyl 912 ″ ″ ″ 2-CH₃O-phenyl 913 ″ ″ ″ 4-CH₃O-phenyl 914 ″ ″ ″ 4-C₂H₅O-phenyl 915 ″ ″ ″ 4-CF₃O-phenyl 916 ″ ″ ″ 4-CN-phenyl 917 ″ ″ ″ 3-NO₂-phenyl 918 ″ ″ ″ 4-NO₂-phenyl 919 F H CH₂ CH₃ 920 ″ ″ ″ C₂H₅ 921 ″ ″ ″ n-C₃H₇ 922 ″ ″ ″ i-C₃H₇ 923 ″ ″ ″ n-C₄H₉ 924 ″ ″ ″ i-C₄H₉ 925 ″ ″ ″ s-C₄H₉ 926 ″ ″ ″ t-C₄H₉ 927 ″ ″ ″ n-C₆H₁₃ 928 ″ ″ ″ CH₂-t-Bu 929 ″ ″ ″ CF₃ 930 ″ ″ ″ C₂F₅ 931 ″ ″ ″ n-C₃F₇ 932 ″ ″ ″ n-C₄F₉ 933 ″ ″ ″ n-C₅F₁₁ 934 ″ ″ ″ n-C₆F₁₃ 935 ″ ″ ″ phenyl 936 ″ ″ ″ 2-F-phenyl 937 ″ ″ ″ 3-F-phenyl 938 ″ ″ ″ 4-F-phenyl 939 ″ ″ ″ 2-Cl-phenyl 940 ″ ″ ″ 3-Cl-phenyl 941 ″ ″ ″ 4-Cl-phenyl 942 ″ ″ ″ 2,4-Cl₂-phenyl 943 ″ ″ ″ 3,4-Cl₂-phenyl 944 ″ ″ ″ 2,5-Cl₂-phenyl 945 ″ ″ ″ 2,6-Cl₂-phenyl 946 ″ ″ ″ 2-CF₃-phenyl 947 ″ ″ ″ 3-CF₃-phenyl 948 ″ ″ ″ 3,5-(CF₃)₂-phenyl 949 ″ ″ ″ 4-CF₃-phenyl 950 ″ ″ ″ 2-CH₃-phenyl 951 ″ ″ ″ 4-CH₃-phenyl 952 ″ ″ ″ 2,4-(CH₃)₂-phenyl 953 ″ ″ ″ 2,6-(CH₃)₂-phenyl 954 ″ ″ ″ 2,4,6-(CH₃)₃-phenyl 955 ″ ″ ″ 2-CH₃O-phenyl 956 ″ ″ ″ 4-CH₃O-phenyl 957 ″ ″ ″ 4-C₂H₅O-phenyl 958 ″ ″ ″ 4-CF₃O-phenyl 959 ″ ″ ″ 4-CN-phenyl 960 ″ ″ ″ 3-NO₂-phenyl 961 ″ ″ ″ 4-NO₂-phenyl 962 F Cl CH₂ CH₃ 963 ″ ″ ″ C₂H₅ 964 ″ ″ ″ n-C₃H₇ 965 ″ ″ ″ i-C₃H₇ 966 ″ ″ ″ n-C₄H₉ 967 ″ ″ ″ i-C₄H₉ 968 ″ ″ ″ s-C₄H₉ 969 ″ ″ ″ t-C₄H₉ 970 ″ ″ ″ n-C₆H₁₃ 971 ″ ″ ″ CH₂-t-Bu 972 ″ ″ ″ CF₃ 973 ″ ″ ″ C₂F₅ 974 ″ ″ ″ n-C₃F₇ 975 ″ ″ ″ n-C₄F₉ 976 ″ ″ ″ n-C₅F₁₁ 977 ″ ″ ″ n-C₆F₁₃ 978 ″ ″ ″ phenyl 979 ″ ″ ″ 2-F-phenyl 980 ″ ″ ″ 3-F-phenyl 981 ″ ″ ″ 4-F-phenyl 982 ″ ″ ″ 2-Cl-phenyl 983 ″ ″ ″ 3-Cl-phenyl 984 ″ ″ ″ 4-Cl-phenyl 985 ″ ″ ″ 2,4-Cl₂-phenyl 986 ″ ″ ″ 3,4-Cl₂-phenyl 987 ″ ″ ″ 2,5-Cl₂-phenyl 988 ″ ″ ″ 2,6-Cl₂-phenyl 989 ″ ″ ″ 2-CF₃-phenyl 990 ″ ″ ″ 3-CF₃-phenyl 991 ″ ″ ″ 3,5-(CF₃)₂-phenyl 992 ″ ″ ″ 4-CF₃-phenyl 993 ″ ″ ″ 2-CH₃-phenyl 994 ″ ″ ″ 4-CH₃-phenyl 995 ″ ″ ″ 2,4-(CH₃)₂-phenyl 996 ″ ″ ″ 2,6-(CH₃)₂-phenyl 997 ″ ″ ″ 2,4,6-(CH₃)₃-phenyl 998 ″ ″ ″ 2-CH₃O-phenyl 999 ″ ″ ″ 4-CH₃O-phenyl 1001 ″ ″ ″ 4-C₂H₅O-phenyl 1002 ″ ″ ″ 4-CF₃O-phenyl 1003 ″ ″ ″ 4-CN-phenyl 1004 ″ ″ ″ 3-NO₂-phenyl 1005 ″ ″ ″ 4-NO₂-phenyl 1006 F F NCOOEt CH₃ 1007 ″ ″ ″ C₂H₅ 1008 ″ ″ ″ n-C₃H₇ 1009 ″ ″ ″ i-C₃H₇ 1010 ″ ″ ″ n-C₄H₉ 1011 ″ ″ ″ i-C₄H₉ 1012 ″ ″ ″ s-C₄H₉ 1013 ″ ″ ″ t-C₄H₉ 1014 ″ ″ ″ n-C₆H₁₃ 1015 ″ ″ ″ CH₂-t-Bu 1016 ″ ″ ″ CF₃ 1017 ″ ″ ″ C₂F₅ 1018 ″ ″ ″ n-C₃F₇ 1019 ″ ″ ″ n-C₄F₉ 1020 ″ ″ ″ n-C₅F₁₁ 1021 ″ ″ ″ n-C₆F₁₃ 1022 ″ ″ ″ phenyl 1023 ″ ″ ″ 2-F-phenyl 1024 ″ ″ ″ 3-F-phenyl 1025 ″ ″ ″ 4-F-phenyl 1026 ″ ″ ″ 2-Cl-phenyl 1027 ″ ″ ″ 3-Cl-phenyl 1028 ″ ″ ″ 4-Cl-phenyl 1029 ″ ″ ″ 2,4-Cl₂-phenyl 1030 ″ ″ ″ 3,4-Cl₂-phenyl 1031 ″ ″ ″ 2,5-Cl₂-phenyl 1032 ″ ″ ″ 2,6-Cl₂-phenyl 1033 ″ ″ ″ 2-CF₃-phenyl 1034 ″ ″ ″ 3-CF₃-phenyl 1035 ″ ″ ″ 3,5-(CF₃)₂-phenyl 1036 ″ ″ ″ 4-CF₃-phenyl 1037 ″ ″ ″ 2-CH₃ 1045 ″ ″ ″ 4-CF₃O-phenyl 1046 ″ ″ ″ 4-CN-phenyl 1047 ″ ″ ″ 3-NO₂-phenyl 1048 ″ ″ ″ 4-NO₂-phenyl

C. FORMULATION EXAMPLES

[0245] a) A dusting powder is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc, as inert substance, and comminuting the mixture in an impact mill.

[0246] b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of active compound, 65 parts by weight of kaolin-containing quartz, as the inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurinate, as wetting and dispersing agent, and grinding the mixture in a pinned disk mill.

[0247] c) A dispersion concentrate which is readily dispersible in water is prepared by mixing 40 parts by weight of active compound with 7 parts by weight of a sulfosuccinic monoester, 2 parts by weight of a sodium ligninsulfonate and 51 parts by weight of water and grinding the mixture to a fineness of below 5 microns in a grinding bead mill.

[0248] d) An emulsifiable concentrate can be prepared from 15 parts by weight of active compound, 75 parts by weight of cyclohexane, as the solvent, and 10 parts by weight of ethoxylated nonylphenol (10 EO), as the emulsifier.

[0249] e) Granules can be prepared from 2 to 15 parts by weight of active compound and an inert granule carrier material, such as attapulgite, pumice granules and/or quartz sand. A suspension of the wettable powder from Example b) having a solids content of 30% is expediently used, and this is sprayed onto the surface of attapulgite granules and the components are dried and mixed intimately. The weight content of the wettable powder is approximately 5% and that of the inert carrier material is approximately 95% of the finished granules.

D. BIOLOGICAL EXAMPLES Example 1 Effect on the Spider Mite Tetranychus urticae

[0250] Cut stems of bean plants (Phaseolus vulgaris) carrying one leaf are transferred into brown glass bottles filled with tap water and subsequently populated with approximately 100 spider mites (Tetranychus urticae). Plant leaf and spider mites are then dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has run off, plants and animals are stored in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity). After 6 days of storage, the mortality of the preparation on all stages of the spider mites is determined. At a concentration of 500 ppm (based on the content of active compound), the preparations of Example Nos. 1, 2, 5, 9, 10, 12, 22, 23, 32, 33, 35, 39, 41, 42, 43, 45, 46, 48, 49, 52, 63, 76, 79, 87, 90, 91, 92, 95, 96, 97, 99, 108, 110, 113, 117,120, 569, 570, 573, 574, 576, 578, 579, 589, 600, 605, 619, 623, 624, 625, 626, 628, 629, 630, 631 effect a mortality of 80-100%.

Example 2 Effect on the Aphid Aphis fabae

[0251] Cut stems of bean plants (Phaseolus vulgaris) carrying one leaf are transferred into brown glass bottles filled with tap water and subsequently populated with approximately 100 aphids (Aphis fabae). Plant leaf and aphids are then dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has run off, plants and animals are stored in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity). After 6 days of storage, the mortality of the preparation on all stages of the aphid is determined. At a concentration of 500 ppm (based on the content of active compound), the preparations of Example Nos. 96 and 103 effect a mortality of 80-100%.

Example 3 Effect on the Egg-Larval Stage of Heliothis virescens

[0252] A Petri dish whose bottom is covered with filter paper and which contains about 5 ml of nutrient medium is prepared. Filter paper sections containing approximately 30 24-hour-old eggs of the tobacco budworm (Heliothis virescens) are dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined and subsequently placed into the Petri dish. A further 200 □l of the aqueous solution are distributed over the nutrient medium. After the Petri dish has been closed, it is stored in a climatized chamber at about 25° C. After 6 days of storage, the mortality of the preparation on the eggs and any larvae hatched from them is determined. At a concentration of 500 ppm (based on the content of active compound), the preparations of Example Nos. 1, 5, 9, 20, 22, 28, 39, 45, 46, 48, 49, 52, 63, 94,103, 116, 568, 567, 573, 579, 589, 619, 623 effect a mortality of 80-100%.

Example 4 Feeding Effect on the Butterfly Larvae Heliothis virescens

[0253] Nutrient medium (freeze-dried cube) is dipped into an aqueous solution of the formulated preparation to be examined and then placed into a Petri dish. Ten L2 larvae of the tobacco budworm (Heliothis virescens) are then added. The Petri dish is then closed with a lid. The effect of the preparation on the larvae is determined after 4 days of storage at about 23° C. At a concentration of 500 ppm (based on the content of active compound), the preparations of Example Nos. 2, 9, 13, 20, 22, 28, 29, 30, 32, 35, 39, 40, 41, 42, 43, 45, 46, 48, 49, 52, 63, 76, 78, 91, 93, 94, 95, 98, 103, 114, 116, 117, 120, 121, 124, 125, 567, 573, 589, 600, 605, 613, 614, 615, 619, 621, 623, 624, 629 effect a larvae mortality of 80-100%.

Example 5 Feeding Effect on the Butterfly Larvae Spodoptera litoralis

[0254] Nutrient medium (freeze-dried cube) is dipped into an aqueous solution of the formulated preparation to be examined and then placed into a Petri dish. Ten L2 larvae of the Egyptian cotton leaf worm (Spodoptera litoralis) are then added. The Petri dish is then closed with a lid. The effect of the preparation on the larvae is determined after 4 days of storage at about 23° C. At a concentration of 500 ppm (based on the content of active compound), the preparations of Example Nos. 5, 9, 12, 28, 29, 30, 35, 39, 40, 41, 42, 43, 45, 46, 48, 52, 63, 87, 90, 91, 92, 94, 97, 98, 99, 100, 103, 107, 113, 117, 120, 125, 566, 567, 573, 574, 589, 600, 613, 614, 619, 626 effect a larvae mortality of 80-100%. 

1. An arylisoxazoline derivative of the formula (I),

in which the symbols and indices are as defined below: X is identical or different a) halogen, cyano, nitro; b) (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl, where the radicals of group b are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen; R¹ is identical or different halogen, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy or cyano; m is 0, 1, 2, 3 or 4; n is 1, 2, 3, 4 or 5; Z is oxygen, sulfur, CH₂or NR²; R² is CN, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, CHO, (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkoxycarbonyl or (CW)NR³R⁴; R³, R⁴ are identical or different H, (C₁-C₆)-alkyl; W is O or S; G is mono- to tetrasubstituted isoxazoline which is attached in the 3-, 4- or 5-position to the adjacent phenyl ring; its pure isomers (optical and geometrical isomers), isomer mixtures, n-oxides and salts suitable for use as pesticides.
 2. A compound of the formula (I) as claimed in claim 1, where the symbols and indices are as defined below: X is halogen, cyano, nitro, (C₁-C₄)-alkyl, (C₁-C₃)-haloalkyl, (C₁-C₄)-alkoxy or (C₁-C₃)-haloalkoxy, m is 0 or 1, n is 1, 2 or 3, Z is oxygen or CH₂, R¹ is H, halogen, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy or (C₁-C₄)-haloalkoxy, G is

t is 0, 1, 2 or 3, R⁵ is identical or different a) halogen, CN, NO₂; b) a straight-chain or branched alkyl group having 1 to 12 carbon atoms, where one or more (CH₂) groups are optionally replaced by —O—, —S(O)—_(0,1,2), —NH—, —NR⁶—, —CO—, —CS—, —CH═CH—, —C≡C—, unsubstituted or substituted aryidiyl, unsubstituted or substituted heterocyclyldiyl, unsubstituted or substituted (C₃-C₈)-cycloalkyl or unsubstituted or substituted (C₃-C₈)-cycloalkenyl, with the proviso that chalcogens may not be adjacent to one another, where two radicals R⁵ together with the atoms of the isoxazoline ring optionally form a 3- to 8-membered ring system and where individual hydrogen atoms are optionally replaced by halogen; c) in the case of two radicals R⁵ located in the □-position, the radicals are also (═Y), where Y is (═O), (═S), (═NOR⁶) or (═CR₂ ⁶); with the proviso that the radical(s) R⁵ together do not comprise more than one ring system having five or more members; R⁶ is (C₁-C₄)-alkyl, unsubstituted or substituted phenyl or unsubstituted or substituted benzyl.
 3. A compound as claimed in claim 2, where the groups R⁵ are as defined below: R⁵ is CN, unsubstituted or substituted phenyl, unsubstituted or substituted phenoxy, (C₁-C₆)-alkyl, (C₁-C₆)-alkenyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-haloalkenyl, -(C₁-C₆)-alkanediyl-aryl, where the aryl group is unsubstituted or substituted and where one —CH₂— unit is optionally replaced by —C(O)—NR¹⁰—, NR¹⁰—(CO), NR¹⁰ or O; R¹⁰ is H, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, unsubstituted or substituted phenyl, unsubstituted or substituted benzyl.
 4. A compound as claimed in one or more of claims 1 to 3, where


5. A compound as claimed in one or more of claims 1 to 4, selected from the group consisting of (I1) to (I28):

where R¹ _(m) and R⁵ are as defined in claim
 2. 6. A process for preparing compounds of the formula (I) as claimed in one or more of claims 1 to 5, where a) to prepare compounds having a 3-isoxazinyl radical, an oxime of the formula (II),

 in which X and Z are as defined for formula (I)  is reacted with a chlorinating agent to give a compound of the formula (III)

 in which Hal is halogen  and then reacted further with an olefin of the formula (IV),

 in which R⁵ and t are as defined above; or b) to prepare compounds having a 5-isoxazinyl radical, an olefin of the formula (VII)

 in which Z and R⁵ _(t) are as defined in claim 2, is reacted with a halogenated oxime of the formula (VII)

 where R⁵ is as defined in claim
 2. 7. A pesticide, comprising at least one compound as claimed in any of claims 1 to 5 and at least one formulation auxiliary.
 8. An insecticidal, acaricidal and/or nematocidal composition as claimed in claim 7, comprising an effective amount of at least one compound as claimed in one or more of claims 1 to 5 together with additives or auxiliaries conventionally used for this application.
 9. A pesticide, comprising an insecticidally, acaricidally and/or nematocidally effective amount of at least one compound as claimed in one or more of claims 1 to 5 and at least one further active compound, together with auxiliaries and additives conventionally used for this application.
 10. A composition for use in timber protection or as a preservative in sealants, in paints, in cooling lubricants for metal working or in drilling and cutting oils, comprising an effective amount of at least one compound as claimed in any of claims 1 to 5 together with the auxiliaries or additives conventionally used for this application.
 11. The use of a compound as claimed in one or more of claims 1 to 5 or of a composition as claimed in claim 7, 8 or 9 for preparing a veterinary medicament.
 12. A process for preparing a composition as claimed in one or more of claims 7 to 11, which comprises combining the active compound and the other additives and formulating them to give a suitable use form.
 13. The use of a compound as claimed in one or more of claims 1 to 5 or of a composition as claimed in one or more of claims 7, 8 and 9 as a timber preservative or as a preservative in sealants, in paints, in cooling lubricants for metal working and/or in drilling and cutting oils.
 14. The use of compounds as claimed in one or more of claims 1 to 5 or of a composition as claimed in one or more of claims 7, 8, 9 and 10 for controlling harmful insects, Acarina, molluscs and nematodes.
 15. A method for controlling harmful insects, Acarina, molluscs and/or nematodes, in which an effective amount of one or more compounds as claimed in one or more of claims 1 to 5 or of a composition as claimed in one or more of claims 7, 8, 9 and 10 is brought into contact with the organisms mentioned.
 16. A method for controlling harmful insects, Acarina, molluscs and/or nematodes as claimed in claim 15, in which an effective amount of a compound as claimed in any of claims 1 to 5 or of a composition as claimed in any of claims 7, 8 and 9 is applied to these organisms or to the plants, areas or substrates infested with them.
 17. Seed, comprising or coated with an effective amount of a compound as claimed in any of claims 1 to 5 or of a composition as claimed in any of claim 7, 8 or
 9. 